Home Vacation Rentals By Owner In Sisters, OR

Showing 80 Of 203 Vacation Rentals
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Exceptional(81)

$227.27

/ Nightly
Condo

Views! 1 Blk to Town,New+Spotless, pets ok- Middle

Sisters, Oregon, United States

ENJOY Sisters best kept secret for vacation rentals in prime location! All you need for comfortable lodging without sacrificing all the creature comforts, that are super clean and well appointed! You will love it! brbrAfraid of driving in the snow No problem! You are 1 BLOCK to the start of downtown for all your needs! Leave your car and walk if you'd like! brbrOne bedroom with king size bed, and a new queen size sofa sleeper in the living room makes this condo comfortable for up to 4 people. Soaring vaulted living room ceilings, light and bright, and hardwood floors throughout. This unit is also ADA compliant. brbrAfter a long day relax on the couch and recliner to watch TV, high speed internet, DVD player and cable TV with Netflix and other shows. brbrLocated next to Pine Meadow Village with mountain and ranch views from this SUPER QUITE condo. It adjoins a beautiful established neighborhood with park like settings, and only a short walk, ONE BLOCK SO Leave your car, to downtown restaurants and shopping. Kitchen with fridge, sink, microwave, dishwasher, range, blender, 2-slice toaster , toaster oven, dishes, silverware, accessories, and a coffee machine with a free pack of Sisters coffee to enjoy. PLUS there is a new washer dryer to use! What a great amenity to have! brbrPets: Under 45 lbs, $35.00 pet fee per pet limit 2. Longer stays will need approval from owner, May be subject to additional fees. Email pet friendly owner to discuss your fur baby before booking. brbrThese units are wonderful! brbrIn the spring and summer months there is a farmers market only one block away with fresh local fruits and vegetables, (we put brand new blenders in each unit to enjoy), and Bi-Mart and Rays grocery store are both a short distance away. brbrThis is one of three new beautiful suites available, there is also available Sisters Executive Suites South, unit 3, and Sisters Executive suite North unit 1. brbrLocated at: 291 S. Pine Meadow St, init 2, Sisters Oregon 97759.
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Sleep 4

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Exceptional(4)

$366.81

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Cabin

FivePine Lodge & Cabins - Classic Cabin

Sisters, Oregon, United States

FivePine Lodge & Cabins is rated one of the top hotels in Oregon. FivePine Lodge & Conference Center is located in the heart of Central Oregon, only 25 minutes from Bend and Redmond, Oregon, 10 minutes from Black Butte Ranch, and 45 minutes from Sunriver. FivePine Lodge is a unique and one of a kind Central Oregon romantic destination and is so much more than just a hotel. With the personal touch of a bed and breakfast, the privacy of romantic, cozy cabins and all the amenities of a resort, FivePine is the ultimate romantic getaway.brOur Classic Cabin, an ideal 680 sq. ft. room, is the perfect getaway for two. Located on the FivePine campus, you are only a short walk to all that we offer, including a walking trail that leads you right to the heart of downtown Sisters. Featured in the Classic Cabin is our luxury king pillow top bed, a 49” flat screen television, fireplace, an Italian tiled shower and a Kohler Purist waterfall soaking tub in our oversized bathroom. Walk through our beautifully designed French-doors to your private patio, offering Adirondack furniture for two. It is the perfect place to kick your feet up and enjoy the refreshing Central Oregon outdoors. brbrCabin Features:brLuxury King Pillow Top BedbrGas FireplacebrWaterfall Soaking TubbrItalian Tile Showerbr49” TV & DVD PlayerbrPatio with Adirondack ChairsbrIn Room French Press Coffee & Tea SelectionbrMicrowavebrMini FridgebrIron & Ironing BoardbrHairdryerbrbrThis cabin type is non-smoking and non-pet.
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Sleep 4

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Exceptional(32)

$646.47

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Private Vacation Home

Stunning Single level Home, Hot Tub, Fenced Yard, Pet Friendly

Sisters, Oregon, United States

Sisters Basecamp br brThis stunning 5 bedroom, 3 bath home is the perfect getaway for guests looking to mix a little relaxation with recreation. br brLight and bright with warm wood accents throughout, stylish decor, comfortable furnishings, and thoughtful amenities, you will feel right at home at Sisters Basecamp. br brRelax in the spacious living room with a plush oversized couch, full-size arcade games, and large mounted flatscreen TV. br brPreparing and gathering for meals will be a breeze in the gorgeous fully equipped kitchen with stainless steel appliances, plenty of counter and cupboard space, and large dining table. The kitchen also has a Smart TV, so the cook in the group doesn't have to miss out on the big game while prepping dinner. We all know everyone always ends up in the kitchen, so turn on the TV, put out some snacks on the kitchen island, and savor this precious time together with loved ones. br brAfter an adventure filled day, retreat to the beautiful and expansive enclosed backyard where the kiddos can get the wiggles out on the trampoline before bedtime, and the adults can unwind around the fire pit with their beverage of choice, or take a relaxing soak in the brand new hot tub. br brStill have some energy to burn Challenge your friends or family to an epic arcade game battle, or a game night at the card table in the living room. br brContent and sleepy - guests will have their choice of 5 comfortable bedrooms to ensure that everyone enjoys a restful night's sleep. br brBedroom 1: Queen Bed brBedroom 2: Kids will go crazy for this Star Wars themed room with Full Sized Daybed with twin trundle brBedroom 3: Full Size Bed with twin futon, toys and games in the closet brBedroom 4: Queen Ensuite with bathtub, Smart TV, desk and chair brBedroom 5: King Ensuite with shower, Smart TV, ceiling fan, and walk-in closet with desk and chair br brWith thoughtful perks like a dishwasher, washer and dryer, a mud room, toys and games, and several designated work areas - perfect for sending a few emails before an early morning tee time at nearby Aspen Lake Golf Course, or if the kids need a quiet place to do some studying before hitting the slopes - everything you need for a success vacation is here! The home is also pet-friendly, so your favorite furry family member can join in on all the fun! br brThis home will be the perfect home base to explore the rustic charm and high desert beauty of Sisters and Black Butte, and in winter months, a 20-minute drive will have you shredding some powder at Hoodoo Ski Resort. br brWe guarantee after one stay, you will be planning your next return to Sisters Basecamp!brbr*Each home is individually owned. Amenities and furnishings are subject to change at any time. For questions on this, please contact our office.br*Fire pit usage is subject to restrictions during the fire season. Please contact or visit online the local fire department or Deschutes County for current fire regulation information.
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Bath 3

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Sleep 12

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$226.93

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Condo

Views! 1 Blk to Town,New+Spotless, pets ok- North

Sisters, Oregon, United States

ENJOY this super popular new Condo in prime Sisters location! All you need for comfortable lodging without sacrificing all the creature comforts, that are super clean and well appointed! brbrAfraid of driving in the snow No problem! You are 1 BLOCK to the start of downtown for all your needs. Leave your car and walk if you'd like! brbrOne bedroom with king size bed, and a new queen size sofa sleeper in the living room makes this condo comfortable for up to 4 people. Soaring vaulted living room ceilings, light and bright, and hardwood floors throughout. After a long day relax on the couch and recliner to watch TV, high speed internet, DVD player and cable TV with Netflix and other shows. brbrLocated next to Pine Meadow Village with mountain and ranch views from this SUPER QUITE condo. It adjoins a beautiful established neighborhood with park like settings, and only a short walk, ONE BLOCK SO Leave your car, to downtown restaurants and shopping. Kitchen with fridge, sink, microwave, dishwasher, range, blender, 2 slice toaster, toaster oven. dishes, silverware, accessories, and a coffee machine with a free pack of Sisters coffee to enjoy. PLUS there is a new washer dryer to use! What a great amenity to have! brbrPets: Under 45 lbs, $35.00 pet fee per pet, limit 2. Longer stays over 3 days will need approval by owner, may be subject to additional fees. Email pet friendly owner to discuss your fur baby before booking brbrThese units are Sisters best kept secret! You will love it! brbrIn the spring and summer months there is a farmers market only one block away with fresh local fruits and vegetables, (we put brand new blenders in each unit to enjoy), and Bi-Mart and Rays grocery store are just a short distance away. brbrThis is one of three new beautiful suites available, there is also available Sisters Executive Suites South, unit 3, and Sisters Executive suite Middle, unit 2 which is ADA compliant. brbrLocated at: 291 S. Pine Meadow St, unit 1, Sisters Oregon 97759.
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Exceptional(6)

$366.1

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Condo

Cozy Sisters Condo | Fireplace, Pool, Spa

Sisters, Oregon, United States

Welcome to our charming upstairs condo nestled in the beautiful town of Sisters, Oregon. This delightful vacation rental offers a perfect blend of comfort and entertainment, making it an ideal retreat for families or groups of friends. brbrAs you step inside, you'll be greeted by a warm and inviting living space adorned with a cozy fireplace, creating the perfect ambiance for those chilly mountain evenings. Relax on the comfortable sofas, unwind with a good book, or gather around the fire for some quality time with your loved ones.brbrThe condo boasts two well-appointed bedrooms designed to provide a restful night's sleep. Both rooms are furnished with cozy, comfortable queen size beds. For additional sleeping arrangements, two twin roll-away beds are also available, ensuring everyone has a comfortable place to lay their heads.brbrOne of the highlights of this vacation rental is the access to the community clubhouse. Step outside and make your way to the clubhouse, where you'll find a pool table, perfect for friendly competitions and creating lasting memories. Additionally, the outdoor seasonal pool offers a refreshing escape during the warmer months, allowing you to soak up the sun and cool off with a rejuvenating swim. And when you're ready to unwind and relax, indulge in the bubbling bliss of the spa, offering a soothing retreat for your tired muscles.brbrThe condo's location is simply unbeatable. Situated within walking distance of downtown Sisters, you'll have easy access to charming shops, delicious restaurants, and local attractions. Explore the town's western flare as you wander through the streets, taking in the unique architecture and vibrant atmosphere. Whether you're seeking outdoor adventures, cultural experiences, or simply a tranquil escape, Sisters has something for everyone.brbrAfter a day of exploration, return to your comfortable retreat, where the western-inspired decor creates a welcoming and authentic atmosphere. From rustic elements to subtle nods to the Old West, you'll feel immersed in the charm of the region. Kick off your boots, relax on the balcony with a glass of wine, and soak in the scenic views of Sisters' breathtaking surroundings.brbrBook your stay in this wonderful upstairs two-bedroom condo today and create unforgettable memories in the heart of Sisters, Oregon.brbrUpon making a reservation please note that signing a rental agreement will be necessary before you are granted access to the property.
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Bath 2

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Sleep 6

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Exceptional(13)

$465.05

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Private Vacation Home

Cozy & Cool & Dog Friendly Cabin in Black Butte Ranch

Sisters, Oregon, United States

Welcome to Acer Haus- your 70's cozy sexy cool dream haus, tucked into the beautiful Deschutes National Forest and in the heart of Black Butte Ranch.brbrAcer Haus is a 70's architectural beauty, with cedar-lined vaulted ceilings and eye poppin' angles. The living/dining is cozy and functional with an open layout that flows into the fully stocked kitchen. There's dining for 6 and lots of lounge space and comfy rugs to chill out in the living room next to the fireplace.brbrAll 3 bedrooms are equipped with king size Nectar mattresses and black out curtains, although you probably won't need them-Black Butte is, well, black, at night. Each bedroom also has a small fan for white noise or extra air flow.brYou'll have a full bath on each floor stocked with Public Goods essentials.brbrThere's a 60 smart tv and wireless bluetooth for entertainment and some classic boardgames and puzzles for the more analog-inclined.brbrThe outdoor space has a large dining table, an outdoor sectional and propane grill. There's also a tie up out front for pups since there are no fenced in spaces.brbrYou're steps away from bike trails that criss cross the ranch, Aspen lake is a stones throw away and is great for sunny picnics. Glaze Meadow has the closest outdoor and indoor pools as well as an outdoor hot tub, just a quick 10 minute walk. Glaze Meadow also has a killer golf course, a bike rental spot or the spa, if thats more your speed.brbrBlack Butte Ranch website has all of the many amenities and hours listed, so thats worth a peek to help plan your trip.
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Sleep 8

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$578.14

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Condo

Lakeview Meadow Retreat

Sisters, Oregon, United States

Summary:brbrPeaceful Black Butte escape with lake views, mountain scenery & walkable diningbrbrbrbrThe Space:brbrTucked into a prime spot at Black Butte Ranch, the Country House Condos offer the best of both worlds—just a short stroll to the Lakeside Bistro, Lodge Restaurant, and nearby amenities, yet peaceful enough for a truly relaxing getaway.brbrbrbrThis end-unit condo showcases stunning views of the lake, open meadow, and distant mountain ridgeline, enjoyed from both inside the home and the private deck. Step inside to an inviting open layout overlooking the dining area, living room, and a beautifully updated kitchen featuring modern appliances and refreshed countertops. The main level also includes a comfortable queen bedroom and a full bathroom.brbrbrbrUpstairs, you’ll find a second queen bedroom with its own ensuite bathroom and dual sinks for added convenience. Whether you're visiting in winter or summer, this home is well-equipped with a cozy wood-burning stove, air conditioning, and WiFi. Plus, enjoy outdoor cooking on the propane BBQ set on the scenic deck any time of year! brbrbrbrLocated in beautiful Black Butte Ranch, this home offers easy access to pools, golf, tennis, pickleball, walking and biking trails, horseback riding, and scenic mountain views. brbrbrbrJust 10 minutes away, downtown Sisters features charming Western-style shops, local restaurants, coffee spots, art galleries, and seasonal events. Outdoor lovers can explore nearby hiking, fishing, and lakes, while the vibrant town of Bend—known for breweries, shopping, and recreation—is only about 40 minutes away. Perfect for both relaxation and adventure!
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Sleep 4

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Exceptional(18)

$436.56

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Cabin

A-Frame Cabin on 4.5 Acres - HOT TUB, Dog Friendly!

Sisters, Oregon, United States

This 2 bedroom Northwest themed A-Frame is the perfect destination for your couples retreat or small family vacation! It is situated on a super peaceful 4.5 acre lot and is only a 7 minute drive to Downtown Sisters. Our cabin sleeps 4 people comfortably in the 2 upstairs bedrooms, has 2 full bathrooms, a stocked kitchen, and a private back patio featuring a brand new hot tub. This is a dog friendly home so you are more than welcome to let your furry friend tag along!brbrThis cozy 2 bedroom A-Frame is the classic landing spot for your Central Oregon getaway. You get the best of both worlds with this location as the home sits on a peaceful and secluded 4.5 acre lot, yet is still just minutes from Downtown Sisters. Downstairs is an open concept layout with the kitchen, dining area, and living room all right next to each other making it the perfect spot for all 4 guests to hangout. The kitchen is well-equipped for our guests to make meals at the home, and the living room is very comfortable with plenty of seating, a stone propane fireplace, and a smart TV for streaming. Also downstairs is a full bathroom & laundry room with a washer/dryer that is available for guests to use.brbrOff of the living room is the back patio that features a brand new hot tub, beautiful concrete dining table, Adirondack chairs, and a propane BBQ. The metal “pool” that is pictured outside is empty so we ask that guests not fill this up as this could be a safety hazard for children. brbrUpstairs you will find another full bathroom (with a shower that is not pictured), plus the 2 bedrooms that feature large vaulted ceilings and 2 Queen Size beds. The master bedroom also has a balcony great for sipping coffee on Summer mornings! This is a dog friendly home so you are more than welcome to let your furry friend tag along!brbrThere are local attractions all around including Downtown Sisters being only a 7 minute drive, and Aspen Lakes Golf Course just 3 minutes away. Don’t hesitate to reach out if you have any questions!brbrAlso, please note that in Central Oregon in the Winter we often have snowy road conditions. To make things simple, we stick to our stated cancellation policy. Please keep this in mind when booking in the Winter months. We also have a similar policy for smoke in the Summer. There’s a chance due to wildfires that there are smokey air conditions during your stay. If evacuations were to take place (extremely rare around here!) then a refund would be given, but other than that we will stick to the stated cancellation policy. Thank you for your understanding!brbrNote about the outdoor wood-burning fire pit: If you use the fire pit, ensure the fire is contained to the metal pit, attended at all times, and that the fire is fully extinguished before leaving it. No fires allowed on the property besides inside the fire pit. No fires between the months of June and September, or during high or extreme fire danger conditions.brbrAbsolute gem!! Beautifully decorated, cozy cabin. They’ve truly thought of everything. Feels like you’re tucked away from everything, yet just a short drive to Sisters. You can stop looking at other listings now because you’ve found the best one out there!! - Review from Mackenize (August, 2023)brbrPiney Camp felt like a warm hug. It was perfect for a peaceful getaway with the family. Kid friendly and cozy. Would definitely recommend! - Review from Brittany (September, 2023)
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Exceptional(70)

$912.5

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Private Vacation Home

Pools, Private Hot Tub & Pool Table. Upscale Lodge

Sisters, Oregon, United States

Welcome to Smiling River Lodge, a 4,191-square-foot custom home sleeping 14. This 4BR/4.5BA Black Butte home features two ground floor suites, bunkroom for eight, and a private hot tub.brbrLIVING AREAbrbrVaulted ceilings glow in the skylit Great Room with floor-to-ceiling stone wood burning fireplace and 65 TV. Entertaining extras include a full-size billiard table, a poker table, and a library of board games.brbrCurl up with a good book in the loft, detailed with a wood-burning fireplace and a foosball and ping-pong table.brbrKITCHEN & DININGbrbrIndulge your inner chef in the gourmet kitchen, complete with ample counter space and stainless steel appliances -- including a double oven. The kitchen bar seats three.brbrGather together beside a wood-burning fireplace in the dining area, furnished with a table for 12.brbrBED & BATHbrbrHighlighted by vaulted ceilings, the primary suite has a king bed, walk-in closet, wood-burning fireplace, and direct hot tub access. The spa-like en-suite bathroom has separate double vanities, a walk-in shower, and a sunken soaking tub.brbrThe second suite includes a queen bed and an en-suite bathroom with a tub/shower combination.brbrA half bath adds convenience downstairs.brbrAlso featuring vaulted ceilings, the third bedroom provides four twin-over-twin bunk beds and a flat-screen TV. The en-suite bathroom features a double vanity, a separate water closet, and a walk-in shower. This bunkroom is on the second floor.brbrThe fourth bedroom, also on second floor, has a king bed and nearby shared bathroom with a tub/shower combination. brbrOUTDOOR AREA & AMENITIESbrbrSurrounded by pines, your expansive deck includes a private tub, gas grill, and dining space as well as a hammock and horseshoe pit on this forested 2.6 acre property. The National Forest is a few hundred yards away, just head out the back door and down the hill West between two houses through the forest access common space.brbrAn easy 8-minute walk, the Glaze Meadow Recreation Center provides a wide array of amenities. Highlights include:brbr- Year-round indoor pool, steam room, and outdoor hot tubbr- Outdoor pools (open Memorial Day to Labor Day)br- Seasonal Bistro with bar and grillbr- Fitness centerbr- Studio with yoga classesbr- Equipment rentalsbr- Pickleball and tennis courtsbr- Bocce ball courts and full basketball courtbr- Bike, Cross Country Ski and equipment rentalsbrbrEXTRA PERKS & MORE DETAILSbrbrPerks include complimentary Wi-Fi, central air-conditioning, YouTube TV (cable), a washer/dryer, and various sleds and bikes.brbrDriveway parking is provided for five vehicles. Street parking is prohibited. Please park only on the pavement.brbrThis two-story home is accessed via a set of three steps at the entryway.brbrThe Ranch no longer collects a per person/day Guest Usage Fee at the Welcome Center. They are now having the property manager collect 13.5% of the rent and remit to the Ranch. This is an extra fee that we collect through VRBO just before check-in. You still need to check-in at the Welcome Center but will not be charged by them.brbrThis home has exterior audio/video cameras in the front and back of house.brbrIf you need anything before, during, or after your stay, we are here to help!brbrEnjoy!brFreddie and Erica Woekel
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Bath 4

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Sleep 14

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$680.74

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Private Vacation Home

Black Butte Ranch Country House 62

Sisters, Oregon, United States

Welcome to Your Relaxing Getaway at Black Butte Ranch.brbrStep into the heart of the Pacific Northwest at Black Butte Ranch, a beloved Western resort rich in history and natural beauty. Originally a working cattle ranch, this iconic destination offers an unbeatable blend of outdoor adventure, family-friendly activities, and upscale amenities.brbrYour stay begins at our beautifully updated Country House Condo, ideally located just steps from the resort’s main lake, Lodge, Kids Recreation Center, and outdoor pool and hot tub. Whether you're looking for adventure or pure relaxation, everything is within easy reach.brbrEndless Recreation at Your DoorstepbrbrBlack Butte Ranch is a year-round playground offering something for everyone:brbr2 Championship Golf Courses, putting course & driving rangebrbrTennis & Pickleball CourtsbrbrMiles of Scenic Walking & Biking TrailsbrbrIndoor & Outdoor PoolsbrbrHorseback Riding at the on-site stablesbrbrLake Activities: Canoeing, paddle boarding, and fishingbrbrSpa & Fitness Center, on-site grocery store, and pro shopbrbrDining Options: From lakeside fine dining to casual bistro farebrbrJust a short 10-minute drive away, the charming town of Sisters awaits with its art galleries, boutiques, and restaurants. For winter fun, Hoodoo Ski Area is only 10 miles away, and nature lovers will enjoy exploring the Metolius River, Camp Sherman, and the ever-popular Wizard Falls Fish Hatchery.brbrComfort & Style InsidebrbrThis spacious two-level condo is designed for comfort and connection:brbrMain Level:brbrQueen bedroom & full bathroombrbrOpen living area with built-in desk, smart TV, and cozy wood stovebrbrHeated tile floors & stunning viewsbrbrFully equipped kitchen & dining area for 6brbrUpstairs:brbrQueen master suite with TV/DVDbrbrSecond bedroom with 2 twins has a barn door for added privacybrbrFull bathroom with washer & dryerbrbrStay connected with free WiFi, and enjoy a warm, pet-friendly welcome — well-behaved dogs stay free. (Please note: no garage parking is available.)brbrCreate Lasting MemoriesbrbrBlack Butte Ranch has been creating unforgettable memories since the 1970s. Whether it’s your first visit or your family’s new tradition, there’s never been a better time to experience the magic of the Ranch.brbrBook your stay today and start your Black Butte tradition.brbrDCCA# 821136
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Bath 2

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Sleep 6

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Exceptional(5)

$491.7

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Private Vacation Home

Peters Cabin Cozy Retreat in Sisters Tollgate Area

Sisters, Oregon, United States

Welcome to our charming vacation rental nestled in the beautiful neighborhood of Tollgate in Sisters, Oregon. This delightful 3-bedroom, 2-bathroom house offers the perfect retreat for your next getaway. With comfortable sleeping arrangements including 2 queen beds, two twin beds, a sleeper sofa, and a queen air mattress, there's plenty of space to accommodate up to 8 guests.brbrAs you step inside, you'll be greeted by the warm and inviting atmosphere that defines this rustic home. The cozy living area is adorned with tasteful furnishings and features a TV, perfect for unwinding after a day of exploration. The fully equipped kitchen provides all the essentials for preparing your favorite meals, and the adjacent dining area offers ample seating for memorable family dinners.brbrOne of the highlights of this vacation rental is the back deck, where you can soak up the sunshine and enjoy the fresh mountain air. Fire up the barbecue grill and savor delicious grilled treats while relishing the serene surroundings.brbrDuring your stay, you'll have access to the fantastic amenities of the community. Take a refreshing dip in the sparkling pool on hot summer days, challenge your friends to a game of basketball, or test your tennis skills on the courts. There's no shortage of activities to keep you entertained throughout your vacation.brbrIn the interest of safety, we want to disclose that the spacing between posts on the upstairs landing area may be wider than standard railings. Please exercise caution and ensure the supervision of children in this area.brbrSisters, Oregon, is renowned for its breathtaking natural beauty and abundant outdoor recreational opportunities. Whether you're an avid hiker, cyclist, or simply enjoy exploring nature, you'll find numerous trails and parks nearby to satisfy your adventurous spirit.brbrWhen you're ready to venture beyond the neighborhood, the charming town of Sisters awaits. Discover quaint shops, art galleries, and delightful restaurants, all within a short distance from your vacation rental.brbrEscape the hustle and bustle of everyday life and indulge in a memorable vacation at our 3-bedroom, 2-bathroom house in the Tollgate neighborhood of Sisters, Oregon. Book your stay today and create cherished memories with your loved ones.brbrUpon making a reservation please note that signing a rental agreement will be necessary before you are granted access to the property.
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