Home Vacation Rentals By Owner In Sisters, OR

Showing 180 Of 203 Vacation Rentals
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Exceptional(25)

$327.77

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Private Vacation Home

Bluegrass home in Crossroads - Pet friendly home just outside of Sisters

Sisters, Oregon, United States

Newly remodeled 2 bedroom 2 bath home just outside of Sisters.  Located on a private, wooded, one acre lot in Crossroads.brbrYour dog will enjoy this vacation as well with a fully fenced front yard.  brbrThis is the enchanted area of the explorers Lewis and Clark, offering miles and miles of rivers, lakes, forest, and stunning mountain peaks.brbrFor the golfers, Aspen Lakes, BIack Butte and Eagle Crest are within 15 miles.brbrFor road cyclists and mountain bikers the trip can start right outside the door, with miles of bike friendly roadway and enough trails to challenge any rider – or take the trail into town.brbrFor the avid fisherman or fisher woman, birder and hiker, the blue-ribbon native trout waters of the Metolius River offer great fishing and unparalleled scenic beauty and relaxation.brbrOr you might want to swim at Camp Sherman, only 20 minutes away, and dip into pools in a bucolic mountain setting.brbrFor those visiting in the winter months, Bluegrass is just 20 minutes from skiing at HooDoo and only an hour from Mt. Bachelor, as well you’ll find miles and miles of trails and cross country skiing and snowmobiling within 10 minutes of the cabin! You can even start your hike or bike ride or cross country ski from the house – the Deschutes National Forest with its extensive network of trails, borders the property.
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Sleep 5

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Exceptional(22)

$356.06

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Private Vacation Home

Cozy Tollgate Cabin Near Trails + Pool

Sisters, Oregon, United States

Nestled in the friendly Tollgate community just minutes from downtown Sisters, Oregon, The Sisters Moose is the perfect affordable getaway for two couples or a small family looking to relax, explore, and enjoy everything Central Oregon has to offer.brThis cozy mountain retreat comfortably sleeps up to 7 guests with 2 bedrooms and 2 bathrooms, offering an open-concept layout with plenty of room to spread out. Guests will enjoy both a spacious family room and a separate TV room — perfect for movie nights, kids, or simply having extra space to unwind after a day of adventure.brThe primary bedroom features a comfortable queen bed, while the second bedroom offers a queen bed plus a set a bunk bed with a twin over double bed, making this home ideal for families, couples traveling together, mountain bikers, or outdoor adventurers.brStep outside and enjoy all the extras that make this home fun and memorable:brYard gamesbrDart boardbrHorseshoe pitbrBikes provided for guest usebrNearby walking and biking trailsbrMiles of surrounding National Forest land to explorebrJust a hop, skip, and a jump down the street, guests also enjoy free access to the seasonal Tollgate community amenities including:brSwimming poolbrTennis courtbrBasketball courtbrChildren’s playgroundbrTollgate is known for its welcoming neighborhood atmosphere where guests can enjoy peaceful walks, kids riding bikes around the loop, and relaxing among the pines.brInside the home you’ll find:brWiFibrDirectTV service in the living roombrDVD players in additional TV areasbrOpen kitchen and gathering spaces perfect for spending time togetherbrFor warmer summer days, the home includes a wall-mounted split-level air conditioning unit in the living room. Please note this is not central A/C.brImportant Notes:brThe pellet stove is not available for guest use.brPool season typically runs from the end of May through mid-September, weather permitting.brTollgate Pool Hours:brLap Swim: 10:00 AM – 12:00 PMbrOpen Swim: 12:00 PM – 7:00 PMbrLap Swim: 7:00 PM – 8:00 PMbrWhether you're visiting Sisters for hiking, mountain biking, skiing, festivals, or simply a quiet weekend getaway in the pines, The Sisters Moose offers a comfortable and affordable home base for your Central Oregon adventure.
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Sleep 7

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Exceptional(11)

$374.05

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Condo

Magical Sisters Retreat 1st Floor 2 Bedroom Condo in Pine Meadow Village

Sisters, Oregon, United States

Let us welcome you to, Magical Sisters Retreat. A calm and relaxing 2 bedroom 2 bath condo located in the Pine Meadow Village neighborhood.  With easy access to Highway 20 and a short walk to downtown; you will be positioned perfectly to enjoy all that Sisters Oregon has to offer. brbrWhen you enter you will be greeted by an open, bright and inviting space. Relax in front of the fire or enjoy your favorite movie on the smart TV.  Enjoy some fresh air while relaxing on the front porch just off the living space.brbrThe culinary enthusiast of your group will enjoy the fully equipped kitchen, including the large fridge, microwave, oven, dishwasher, dishes, cookware, silverware, and toaster.  The open layout means they won't miss a moment of the memories being made. brbrDown the hall the first door to the left has the laundry room with a full size washer and dryer.  Tide pods are provided for your convenience.  Next is the first of the 2 full bathrooms. followed by the second bedroom that includes a King mattress, dresser and closet for storage.  The Primary bedroom is the perfect getaway.  It comes equipped with a King mattress, walk-in closet, full ensuite bathroom with 2 sinks, and it's own private porch where you can step outside to enjoy your morning cup of coffee. brbrMagical Sisters Retreat is the place you have been looking for to enjoy some time away from rush and stress of your everyday life.  A great place for friends to laugh or for a  couple to create lasting memories.
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Exceptional(51)

$397.44

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Condo

Big Mt View Condo View of the Mountains in Sisters, A/C, Gas Fireplace

Sisters, Oregon, United States

Park the car and walk or bike to everything in town, mountain views and A/C. Come to Sisters and take in the views of four mountains and pond w/seasonal fountain from this condo. It is on the west edge of Sisters and only a few blocks to the heart of downtown Sisters to shop, dine, browse. Year round spa and seasonal pool privileges are included in this rental and are right next door, tennis courts are just two blocks. brbrDog friendly for a small to medium size dog up to 35 pounds only.brbrThis condo features fully equipped kitchen, complete w/ dishwasher, microwave, toaster, coffee maker, everything you`ll need to cook to your heart`s desire, all linens provided, one car garage for your use. Light and bright with lots of windows, vaulted ceilings and a cozy gas fireplace in the living room make this condo inviting. This is a second level unit w/ 2 bdrm., (1 king, 1 queen), 2 baths, one with tub shower and one with shower only. There is a queen air bed available also which will accommodate 2 more. TV w/cable, DVD player,  AC, washer and dryer for your convenience, and garage access available to guests.brbrQuiet hours apply, 10 p.m. to 8 a.m.brbr1 King bed in master bedroom, queen bed in second bedroom, 1 queen airbed available.brbrbrbr** The Club House including the pool and spa are not managed by Sisters Vacation Rentals.  We cannot guarantee availability.
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Exceptional(29)

$224.14

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Private Vacation Home

Sisters Home Lower - One bedroom/One bath - Sleeps upto 5

Sisters, Oregon, United States

Previously known as Sisters Home Lower, Sisters Retreat Lower offers a clean, modern space perfect for travelers looking to explore the beauty and charm of Sisters, Oregon. This ground-level one-bedroom unit is designed for those who plan to spend their time adventuring, dining, and enjoying everything the town and surrounding wilderness have to offer.brbrPlease Note: This unit does not have a full kitchen.brThere is no sink or stove, but the unit is equipped with a mini fridge, toaster oven, microwave, and coffee maker—perfect for simple meals or leftovers from one of the many amazing restaurants just steps away.brbrLocation Highlights:brbrA short walk to downtown Sisters—restaurants, coffee shops, and boutique shoppingbrClose to outdoor adventures like hiking, biking, and skiing at Mt. HoodoobrOn-site parking and a peaceful neighborhood settingbrThis suite comfortably accommodates up to 5 guests, with cozy sleeping arrangements and a welcoming atmosphere. While there is no laundry on-site, everything else you need for a relaxing home base is here.brbrAdditional Info:brbrThis is one of two units on the property (Sisters Suites Lower & Upper)brOne well-behaved dog is welcomebrA signed rental agreement is required prior to check-inbrWhether you’re here to explore the trails, hit the slopes, or simply soak in the town’s small-town charm, Sisters Retreat Lower is your perfect launchpad.
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Exceptional(7)

$282.21

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Cabin

Wooden A-Frame Cabin Nestled in the Tall Pines

Sisters, Oregon, United States

Relax with the whole family at this peaceful cabin in the woods. 'Your Sisters Cabin' is geared towards fun and relaxation for the whole family. We've crafted the spaces to help adults and children take a load off and enjoy each others company. We've curated the cabin's amenities to help you enjoy the space, the neighborhood and all that the Sisters area has to offer. From an easy to use wood stove to a beautiful backyard retreat, fully stocked kitchen and comfortable beds.brbrThis cozy wood cabin will wrap you in her embrace. Enjoy the beautiful seasons in Sisters from your living room or furnished sunroom where you can take in the snowy sights or enjoy the warm glow of the sun. This cabin offers two bedrooms with queens and a third open loft space outfitted with two twin beds and a play area (note: no door to third bedroom/loft). brbrPerfect for after an activity filled day, find comfortable beds, inviting sitting areas, family board games, toys and two smart TVs with the ability to connect to your favorite app. Your Sisters Cabin is child-friendly with a fun lofted bed with slide and a toy area and infant friendly as well. Enjoy the large patio and huge grassy backyard, fully fenced and ready for family fun and furnished seasonally for you to enjoy. We also have various sized bikes with baby seat attachment, an infant carrier/hiking backpack and a jogging stroller for your use.brbrOur two-car garage will keep your cars safe and protected from the elements as well as provide an area to store skis, bikes and other toys.brbr2.7 miles to Sisters, 20 miles to Hoodoo ski area and surrounded by hiking and biking trails, sno-parks and lakes and rivers.
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Sleep 6

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Exceptional(2)

$657.0

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Cabin

Enjoy Dakota House! A modern. Family-friendly. 4bdr cabin @ Black Butte Ranch

Sisters, Oregon, United States

Relax with the whole family at this peaceful cabin that offers the best of resort living in a private setting. Recently renovated in a modern cabin chic. This is not your average rental. Thoughtful design choices throughout with high end comfort. Lovely views from nearly every window, this cabin sleeps up to ten people. This home is ideally located sitting between the Paulina Springs and South Meadow pools. Across the street begins national forest trails. And you'll love the five minute walk to Aspen Lake and the views from South Meadow where the horses graze under the view of three spectacular mountains. brbrbrThe spacebrNature meets luxury in this highly intentional space. The cabin is nestled between two aspen groves providing privacy and views. The bedrooms are outfitted with Helix mattresses linens from Frette, Boll and Branch and Parachute. This cozy 4 bed/ 2.5 bathroom cabin has four separate bedrooms with one king (master), one queen, and two sets of bunk beds (four beds) in the kids room. The fourth bedroom is a separate tv room/ library that has a couch that converts to a queen bed (Room and Board) One huge bathroom is adjacent to the master (shower). A powder room off the living room and a smaller jack. And jill bathroom on the second floor (bath and shower). brbrThere is a fireplace, couch and chairs for leisure in the living room, plus a dining area, and a fully outfitted kitchen for preparing meals. The high speed internet and two tv's (one frame tv in great room) and one larger tv in tv room/ library. Both are perfect for streaming your favorite shows and movies.brbrThere are outdoor dining and chairs to take in the natural splendor. And of course a grill. brbrbrGuest accessbrGuest will have access to all the amenities Black Butte Ranch has to offer. Sauna. Hot tub Two Golf Courses. Four pools. Tennis courts. Pickle ball. And seriously good food at the Scandanavian lodge. brbrOther things to notebrAlso, please note that in Central Oregon Winters we often have snowy road conditions. We can also have smoke in the late summer and early fall. To make things simple, we stick to our stated cancellation policy. Please keep this in mind when booking in the Winter months. Thank you for your understanding!brbrApologies. We do not accept dogs at Dakota House.
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Exceptional(6)

$906.94

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Lodge

Spacious 6-bed allergy-friendly home with AC - Walk to Glaze Meadow Rec Center

Sisters, Oregon, United States

Significant effort has been made to make the home comfortable for those with particular allergen sensitivity, including mobile air filters (Austin brand), organic cotton mattresses (Avocado Green brand), and organic latex ('Sleep on Latex' brand) mattresses. Organic cotton pillows, sheets, and towels are stocked in the home. Only fragrance and allergen free cleaning products are used. Furnishings are free of flame retardants.brbrThe home, which was built in 2020, was designed with the intent to maximize natural light from large windows throughout the home, offering pleasant views of the surrounding trees and natural landscape. brbrBedroom setup as follows:brDownstairs Bunkroom - full over full bunk and twin over twin bunkbrDownstairs Bedroom - queen bedbrUpstairs Bedroom 1- two twin bedsbrUpstairs Bedroom 2 - queen and toddler bedbrUpstairs Bedroom 3 - full size bedbrUpstairs Master - queen bedbrNuna Pack and Play available for usebrbrFull kitchen with standard appliances and equipment. Two picnic tables on the rear deck for outdoor dining. brbrOne of the unique features of this home is the location. The Glaze Meadow Recreation Center is within walking distance and has a pool, hot tub, fitness center, bike rental, sports shop, and other amenities. The Ranch bike path is conveniently accessible immediately to the rear of the home. The bike path is about 23 miles in total, weaving through the Ranch. brbrNote: The Ranch used to collect a daily use fee when you arrived at the welcome center. Going forward a resort fee is assessed as percentage of the rent amount. This amount will be invoiced to you separately at the conclusion of the booking.
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Sleep 18

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$423.73

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Private Vacation Home

Two Units, One Stay | Perfect for Groups

Sisters, Oregon, United States

Stay Together in Sisters – Entire Building Rental (Upper + Lower)brBring your group together and enjoy the comfort of having both Sisters Retreat Upper and Sisters Retreat Lower all to yourselves. This unique combo stay offers the perfect setup for families, friends, or small groups who want to stay close—while still having their own space.brLocated just a short walk from downtown Sisters, you’ll have easy access to local coffee shops, restaurants, boutiques, and seasonal events. Leave the car behind and enjoy the charm of this walkable mountain town.brTogether, the two units comfortably accommodate up to 7 guests, making it an ideal choice for group getaways, or family gatherings. Each unit offers a bright, modern space designed for comfort and relaxation after a day of exploring Central Oregon.brWhy Guests Love This Combo Stay:brRent the entire building for added privacybrPerfect for groups who want space + togethernessbrWalkable to downtown Sisters shops and diningbrEasy access to hiking, biking, and outdoor adventuresbrAmple parking for multiple vehiclesbrThe Layout:brUpper unit is equipped with a full kitchen, full bathroom, walk-in closet, Queen size bed, and a sleeper sofa. A full size washer and dryer are also available.brLower Unit is equipped with a kitchenette, full bathroom, Queen size bed, and a sleeper sofa.brBoth units have a living space with large smart TV’s, and wifi.brPlease note: These units are designed for convenience and comfort while enjoying all that Sisters has to offer. There is a full kitchen in the upper unit with a small kitchenette in the downstairs unit. brPet Policy: Up to one dog per unit is welcome.brWhether you're here for a weekend escape, an event in town, or outdoor adventure, this combined retreat gives your group the space, flexibility, and location to make the most of your stay.brImportant: A rental agreement must be signed prior to receiving access to the property.
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Sleep 7

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Exceptional(31)

$657.58

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Private Vacation Home

5 Bedroom 3 Bath, Cul-de-sac, Black Butte Ranch, excellent location

Sisters, Oregon, United States

Black Butte Ranch no longer charges per person/per day recreational fees when checking in at Welcome Center. These are included in your VRBO booking.brbrBlack Butte Ranch Cabin: Five Bedroom, 3 Bath, Sleeps 10. brGolf Home 175 - Glacier Lily off Hawks BeardbrGolfing, Biking, Swimming, Hiking, Pickleball, TennisbrbrThis double A- Frame chalet with its spacious decks is located near Big Meadow Golf course and is on a quiet cul-de-sac in the lovely pines, just a few minutes from Paulina Pool, Lakeside Facilities, tennis courts, Big Meadow clubhouse, the playground and the sports field.brbrOn the main floor is an open kitchen/dining/living room with river rock fireplace and spacious decks on two sides of the house. Also on this floor are a bedroom with king, and a bath w/ shower. The living room has comfortable leather seating, flat Screen TV and WiFi. House has heat pump air conditioning.brbrOn the second floor are four bedrooms. Two east wing rooms share a Jack and Jill bathroom. One room has a double bed and one has two twin beds. brIn the west wing two queen rooms and a full bath with shower/tub/double vanity.brbrEnjoy outdoor dinning with friends and family while watching children play together. Off the deck there is an open space for lasso golf, bocce ball or horse shoes and there is a ping pong table in the garage. brbrWe are in an outstanding location with current decor and well-appointed smoke-free environment. This popular sunny home is located on a forested half acre, quiet cul-de-sac with access to the bike path and golf course. Gateway to miles through the great outdoors at Black Butte Ranch, Quaking Aspen, Ponderosa Pines and snow-capped mountains. It is the perfect home for a large family or families with plenty of privacy and space.brbrBlack Butte Ranch was developed in the 1970's and provides a safe a secure area for your family to venture out on their own. We are a gated community and have multiple golf courses, four large pools, nineteen tennis courts and miles of bike paths. It is a working ranch with cattle and horses. Horseback riding is available either individual or by group. Tennis courts are located throughout the ranch in multiple locations. Bike, tennis, golf and ski rentals are available.brbrWe have a beautiful lodge that looks out on a lake and multiple mountains. Fine dining is available at the lodge, pool side dining, and a grill at the Pro shop. We also have canoes and kayak available for rental. We are located 20 minutes from Hoodoo ski resort and 30 minutes from Bend and Mount Bachelor is located close by.brbrBicycles: There are 5 bicycles of varying sizes in the garage. Feel free to use at your own risk. The bicycles are not proactively maintained. Helmets are required on the ranch and not provided. High quality bicycle rentals are available at Glaze Meadow Rec Center: 541-595-5877.brbrbrbrDCCA #000991brbr
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Sleep 10

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Exceptional(6)

$371.95

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Condo

Fourth Sisters Bliss 2 bedroom 2 bath w/ fireplace

Sisters, Oregon, United States

Sitting just off from the historical downtown of Sisters, nestled in the trees, this delightful condo offers a perfect blend of comfort and entertainment, making it an ideal retreat for all. brbrWhen you enter this upstairs condo you will immediately notice the clean and cozy feel it provides. From the decor to the furniture to the wood fireplace, it all provides the perfect environment to be a home away from home. brbrThe two bedrooms offer a getaway space of their very own as each bedroom features warm inviting decor, an ensuite bathroom and personal television. The main bedroom features a luxurious queen bed, while the second bedroom offers an ultra comfortable king bed. Each will be a welcome resting place after a day of enjoying all that Sister’s has to offer.brbrThroughout the rest of the condo you will find all the necessities and conveniences of home that you will need to prepare your meals, play games, unwind, and enjoy time with family and friends. Being in this condominium community, you will also have access to all the onsite amenities such as the seasonal pool and hot tub.brbrThis condo's location is simply unbeatable. Being within walking distance of downtown Sisters, you'll have easy access to charming shops, delicious restaurants, local attractions, and numerous walking trails. Whether you're seeking outdoor adventures, cultural experiences, or simply a tranquil escape, Sisters has something for everyone.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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$413.18

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Cabin

FivePine Lodge & Cabins - Serenity 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.brAt 680 sq. ft., our Serenity Cabins are an oasis of relaxation and tranquility. Couples will enjoy this romantic retreat, situated along the edge of the Deschutes National Forest and featuring a private patio. Thoughtfully designed for two, this cabin features a king size deluxe pillow top bed, 65” flat screen TV and daily delivery of our Deluxe Coffee & Tea Service + mimosas. Surrender to ultimate relaxation with our custom glass rainfall shower, featuring triple body sprayers and a cascading waterfall against the backdrop of the warm glow of your 3 sided fireplace. Tucked between the fireplace and a forest view window, you will find an enchanting cast iron pedestal soaking tub with river stone accents and the irresistible allure of pure luxury. brbrCabin Features:brLuxury King Pillow Top BedbrThree-Sided Stone Gas FireplacebrCast Iron Pedestal Soaking TubbrTriple Head Italian Tile Showerbr65” TV & DVD PlayerbrPatio with Adirondak ChairsbrDeluxe Coffee & Mimosa Delivery with Baked Goods & Fresh FruitbrIn Room French Press Coffee & Tea SelectionbrMicrowavebrMini FridgebrIron & Ironing BoardbrHairdryer brbrThis cabin type is non-smoking and non-pet.
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