Vacation Rentals By Owner In Lee, MA

Showing 72 Of 72 Vacation Rentals

$266.3

Berkshires Summer Rental - Lee/Lenox

Lee, Massachusetts, United States

Sunny three bedroom condo available for summer rental , with two full baths. Shaded front porch and sunny rear deck with BBQ. Rental is fully furnished with linens. Well stocked kitchen- includes dishes, cookware, utensils, with microwave, toaster oven and dishwasher. Rental also includes air-conditioning, cable TV, WiFi , washer/dryer, and ceiling fans. Heated pool and tennis courts onsite. Near Tanglewood, Shakespeare & Company, Jacobs Pillow, and Kripalu. Close by are lakes, hiking and October Mountain State Forest. This spacious end unit is perfect for your summer vacation. Minimum 1 month rental, will give a discount for a three month rental.

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Exceptional(1)

$240.16

/ Nightly

Apartment

Downtown Gateway to the Berkshires. Walk to Everything.

Lee, Massachusetts, United States

Experience the beauty of the Berkshires. Newly renovated two bedroom retreat in downtown, Lee. Steps from all the restaurants & shops. Equipped with a brand-new eat in kitchen with an array of cooking essentials such as pots, pans, cooking utensils, glassware, flatware and dishes. Two private bedrooms both with a comfortable queen beds. This unit has natural light with central heat & central air providing a relaxed environment. The living room features a comfortable couch and a flat screen TV for relaxing. Wi-Fi is available throughout the space. All linens and towels are provided.brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Tanglewood, Jacobs Pillow, Norman Rockwell Museum, Hancock Shaker Village, Jiminy Peak Mountain Resort. The Berkshires is a must for anyone looking to escape to nature. There are endless mountain, lakes, and woods here to enjoy a wide range of outdoor activities, like biking, fishing and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments, along with great seasonal Farmers markets. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else.

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Bath

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Exceptional(98)

$994.13

/ Nightly

Private Vacation Home

Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!

Lee, Massachusetts, United States

Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tanglewood, Stockbridge, Jacob’s Pillow, Mount Greylock, Rail to Trails, October Mountain, the Appalachian Trail, 5 different ski mountains, Great Barrington, antiquing and shopping, and the world’s best sweets at Peace, Love & Chocolate. Three minutes to Lee town center, 6 minutes to the Lee outlets, and 7 minutes to both Stockbridge and Lenox. With 4 bedrooms and a Bunk Room, the house can sleep 12 people in beds, and 14 including a pullout sofa bed. brbrDescriptionbrFrom the moment you walk in to a wall of westerly facing windows full of afternoon sun and a Great Room with a 32ft ceiling, it is relax time. Comfortably furnished and well appointed with all the touches of home, you have multiple ways to relax indoors or out. You can flop down on either of the overstuffed club chairs or couch and put your feet up on an ottoman, go upstairs to the balcony and curl up with a book, retreat to your bedroom and take a nap on a firm but plush mattress, sit on the deck and watch as the sun dips into the trees, or bird watch at one of the feeders.brbrFirst floor:brThe entire 1st floor is an open floor plan designed for family living and friend getaways, entertaining and free flow of movement. There is streaming natural light with a West-facing Great Room and dining area, hardwood floors in all the common areas and hallways, a floor-to-ceiling fireplace, and a walk thru kitchen with stainless steel Bosch and Frigidaire appliances, gas range and granite countertops. The dining area has a large farm table that seats 10 very comfortably (with 12 total spindle-back chairs, for extra guests) and a breakfast bar that has three swivel stools. There are two bedrooms on the ground floor: a bunk room with 2 solid-wood, sturdy, twin bunk beds that sleep 4 (kids much more comfortably but absolutely can fit adults); and a queen room with a sleigh bed and a dressing table (made by Chip’s grandfather). These bedrooms share a large full bathroom and there is a powder room down the hall. All of the bedrooms are carpeted.brSecond floor:brWhen you climb the extra-wide staircase to the 2nd floor, you are treated to a view overlooking the first floor, the soaring timber ceilings and a loft-style common area. You can relax on the sofa or in an overstuffed beanbag, challenge your housemate to a game of foosball on our full size table, listen to music via Alexa on Harmon Kardon speakers, or choose from any variety of puzzles and boardgames. On the north side of the house are two spacious bedrooms with a full bath between them. One bedroom has a queen sleigh bed with a west facing view over the large deck and backyard, and a true old-fashioned wicker rocking chair. The second bedroom has two twin beds with an easterly exposure looking out over the wildflower garden. On the entire South side of the house on the second floor is the master suite. This is a breathtaking room with a cathedral ceiling, a cozy sitting area furnished with club chairs and settee, an ensuite bathroom with double sinks and a gorgeous claw foot tub, and a walk in closet with plenty of space. brbrAmenities and Decor:brThe house is well appointed throughout, with a mixture of mid- and late-19th century antiques and contemporary furniture. Behind the closed panels next to the fireplace you will find a 55” 4K SmartTV, fully equipped with cable, 4K Apple TV, Netflix, Hulu, Max and AmazonPrime video. The kitchen and pantry have everything you need to make a dinner for 2 or 12, from spices and baking needs to blenders and serving platters. Additional amenities include: Pillow-top mattresses, down-alternative comforters, pillows, 100% cotton sheets and duvets (flannel for winter!), hair dryers, towels, washer/dryer, dishwasher, Braun coffee brewer, coffee press, Keurig coffee maker, toaster oven, food processor, pots, pans, slow cooker, blender, baking and serving dishes, knives and utensils. The basement also has a Peloton, a rower and space for the kids to watch TV and play games. Basic spices and baking ingredients are available, as well as condiments (tho many prefer to buy their own). Iron/Ironing board; mudroom; 400mbs wi-fi for multiple workers to stream simultaneously, smart TV, Alexa and speakers; apple TV, foosball; board games.brbrProperty: 2+ acres, well set back from the road, huge yard and back deck to play, grill, or sit around a fire pit. 12 Adirondack chairs, 4 loungers for sunbathing, organic vegetable garden for use of fresh produce — we trade free veggies for weeding and watering. :-)brbrLocation and things to do:brbrFor Spring, Summer and Fall: 5 mins to laurel lake, 15 mins to the Appalachian Trail access, Hiking, fishing, biking, water sports, golfing and other outdoor activities abound! 10 minutes to Tanglewood and Berkshire Theater Company, less than 10 minutes to Lee, Lenox and Stockbridge for antiquing, fabulous dining, and more New England charm.brbrFor the diehard skier, we are a 15 minutes from Butternut and Bosquet, 20 minutes to Otis Ridge (nighttime skiing!), 30 minutes from Catamount and 40mins from Jiminy Peak. In one 3-night stay, you could ski 5 mountains! There is also plenty of wide open space nearby to cross country ski and snowshoe, for those intrepid explorers.

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$350.43

/ Nightly

Apartment

Berkshire Holiday Home. 2-bedroom house/apartment in peaceful Lee.

Lee, Massachusetts, United States

Nestled in Lee, this lovely apartment offers a peaceful retreat for guests seeking comfort and convenience. With two cozy bedrooms featuring queen beds, everyone can enjoy a restful night’s sleep. The apartment includes two bathrooms, each equipped with a refreshing shower to start your day right. Sleep well in air-conditioned bedrooms. Whether you’re relaxing indoors or exploring nearby, this quaint spot provides a welcoming base. Make your holiday one for the books with a stay at our place.brbrThis house was built in 1789 and has been recently renovated. This apartment is the entire front house with a bedroom/bath on the first floor and a bedroom/bath on the second. There is a living room downstairs and a small study upstairs. brbrThere is a large patio and fish pond in the backyard for you to enjoy.

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$473.65

/ Nightly

Private Vacation Home

Spacious Central Berkshires Home for Groups

Lee, Massachusetts, United States

Welcome to Laurel House Place, your beautifully renovated home in the charming town of Lee, the gateway to the Berkshires! Whether you're planning a peaceful getaway, a cultural adventure, or a cozy family gathering, our home is the perfect place to make lasting memories.brbrStep outside to your private backyard, where you can enjoy the fresh Berkshire air. Fire up the BBQ grill for an evening cookout and gather around the patio table for outdoor dining.brGuest AccessbrbrYou will have private access to the entire home, including the spacious backyard and patio area. Make yourselves at home!brThe NeighborhoodbrbrOur prime location puts the best of the Berkshires at your fingertips. We are just a short drive from world-renowned cultural venues like Tanglewood, the Berkshire Theater Festival, and Jacob's Pillow. For shopping, the Lee Premium Outlets are minutes away.brOutdoor enthusiasts will find golf, tennis, skiing, and swimming all nearby. In the winter, enjoy easy access to ski resorts like Catamount, Bousquet Mountain, and Jiminy Peak. During the summer, you can visit Sandy Beach at Lake Laurel, just a 3-minute drive away. As our guest, you have access by simply showing your paid reservation.brGetting AroundbrParking for up to four vehicles is provided directly at the house. To ensure space for everyone, please park two cars side-by-side in the designated area, with two additional cars parked directly behind them.brImportant Informationbrbr Our home is located on Route 20, and you may hear some noise from the road. Running the A/C units can help mute the sound.brbr A shed is available for storage; however, please note that use is at your own risk.brbr Please remember to show your reservation confirmation for access to Sandy Beach at Lake Laurel.

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Exceptional(24)

$892.05

/ Nightly

Private Vacation Home

Amazing Backyard Escape, 10 Minutes from Stockbridge | Cordelia by AvantStay

Lee, Massachusetts, United States

Experience the beauty of the Berkshires from Cordelia, your charming Massachusetts home with a chic cottage style and romantic outdoor spaces. Head to the backyard to find a brick patio and picturesque dining table that makes setting up an Insta-worthy spread a breeze. Gather around the firepit, doze off in the hammock, or play a round of cornhole in the yard. Inside, Cordelia welcomes you with a fireplace and TV in the front living room, a formal dining room, and a country-style kitchen with unique antique pieces. Spread out between five bedrooms before grabbing a glass of wine for a soak in the clawfoot tub upstairs. When you're ready, the Berkshires are packed with more outdoor activities, views, hikes, museums, and art exhibits than you could ever hope to see in one visit. We hope that means we'll be welcoming you more than once!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrLocal Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain ResortbrbrVisiting the Berkshires is a must for anyone looking to pair a gorgeous natural landscape with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods here makes it easy to enjoy a wide range of outdoor activities, from rafting and fishing to ziplining and hiking. Stunning in any season, this region is famous for its food scene, which values local ingredients, and you’ll find many farm-to-table establishments in the southern areas. Explore classic New England architecture, a growing array of performing arts, and dozens of towns and trails. The Berkshires are waiting with variety and beauty you won’t find anywhere else.brbrHome Truths:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home does not have AC.br- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.br- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.brbrThis home comes with a pack n' play travel crib and a high chair available.brbr---brbrThe room configuration is as follows:brPrimary Bedroom: King bed w/ ensuitebrBedroom 2: Queen bedbrBedroom 3: Queen bedbrBedroom 4: King bedbrBedroom 5: Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. All bookings over 30 days require a security deposit.brbrWe report and prosecute all Credit Card Fraud.

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$261.38

/ Nightly

Private Vacation Home

stylish Berkshires Retreat

Lee, Massachusetts, United States

Stay comfortably in Lee at this 2-bedroom house. The space features two queen beds, offering plenty of room for a restful night. Guests can enjoy a welcoming atmosphere with heating and window air conditioning to keep things just right. A single bathroom includes a hair dryer for convenience. Whether you’re relaxing indoors or planning your next adventure, this terrific house provides a fantastic spot to unwind. A great place to call homebase while you're away, we hope you enjoy your stay.

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Exceptional(9)

$413.25

/ Nightly

Private Vacation Home

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee, Massachusetts, United States

Enjoy all the Berkshires has to offer from this charming 3BR/2BA home base for up to 10 people just 5 minutes from downtown Lenox! Located in a scenic, quiet neighborhood ideal for walking and relaxing, it’s the perfect location to explore performing arts, museums, outdoor activities, and the quaint village centers nearby.brbrTop 4 Ski ResortsbrBousquet Mountain: 7.3 milesbrSki Butternut: 15.5 milesbrOtis Ridge Ski Area: 14.4 milesbrJiminy Peak Mountain Resort: 21.5 milesbrbrLenox Center – 5.8 milesbrTanglewood – 4.3 milesbrJacobs Pillow – 10.5 milesbrbrInside, you’ll find hardwood floors, a spacious and exceptionally well-equipped kitchen with plenty of counter space, and attractive furnishings throughout. The main level includes a living room with TV, a dining room (seats 10), a breakfast area, a family room off the kitchen, and a full shower bath. Patio doors open to a large deck overlooking a level backyard perfect for lawn games and outdoor dining.brbrUpstairs has a large bedroom with one queen bed and two twin beds, a second bedroom with a queen bed, and a third with a full bed. There’s also a full bath with tub/shower. A queen sleeper sofa and full bath on the main level allow for one-floor living if desired.brbrWe welcome well-behaved dogs on a case-by-case basis for a $65 fee per dog. Please message us for approval before booking.brbrYour stay includes access to a shed full of lawn games, toys, chairs, and more. We provide a portable crib, high chair, dog crate, and more. Just ask!brbrYou’ll enjoy full access to the house (except basement/garage), with plenty of parking in the driveway (6–8 cars). Contactless check-in is available, and our property management team is available 7 days a week for any assistance.brbrThis home is a thoughtfully outfitted short-term rental not cluttered with owner possessions and is professionally cleaned with green products after each stay.

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Exceptional(13)

$204.44

/ Nightly

Hotel

Resort Stay with Arcade, Heated Pool, Sports Courts & Family Perks

Lee, Massachusetts, United States

Escape to the Berkshires! Experience hiking, boating, and skiing at our doorstep. Nearby, enjoy the Norman Rockwell Museum, Tanglewood, and the Appalachian Trail. Perfect for families and nature lovers.brbrThis listing is for a room within a hotel.brbr✦ Your room is 1016 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, high definition TV, available with Premium cable, and Standard cable, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Public or shared fitness center open from 6:00AM to 11:00PM, available in the property.brbr✦ Indoor pool is available, opened from 8:00AM to 10:00PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $12.50 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are not allowed.brbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

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Exceptional(6)

$204.44

/ Nightly

Hotel

Scenic Escape: Full Kitchen, Pools, Game Room & Outdoor Fun

Lee, Massachusetts, United States

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Exceptional(8)

$204.44

/ Nightly

Hotel

Relaxing Getaway: Pools, Games & Movie Nights

Lee, Massachusetts, United States

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Exceptional(7)

$525.5

/ Nightly

Private Vacation Home

Stonebridge Cabin: Modern Amenities, Enjoy Nature!

Lee, Massachusetts, United States

Summary:brbrOur quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort of a home away from home. Only 5 minutes from town and in the heart of the Berkshires, this cozy cabin is a perfect escape from everyday life. Enjoy the fully appointed trappings of modernity—high-speed internet, a beautifully updated and well-stocked kitchen, hot tub, brand new stylish and comfortable furnishings, TV room, and more!brbrbrbrFind us on social media: @stonebridgecabinbrbrbrbrThe Space:brbrThis newly renovated, beautifully designed, and tastefully decorated home can accommodate 8 guests in 4 bedrooms and 2 bathrooms.brbrbrbrOur brand new, fully-stocked, and modern kitchen has all new stainless steel appliances, including a gas range for cooking, and a dishwasher to make cleaning up a breeze. We’ve stocked all the cooking and serving necessities, including cookware, pots, pans, plates, cups, silverware, and more. And of course, a coffee pot is available for your morning coffee. There are plenty of seats at the dining table to enjoy meals with family and friends. brbrbrbrTo help with sleeping arrangements, there are four bedrooms in total:brbr-Two bedrooms on the main level, each with queen size bedsbrbr-One bedroom upstairs with a queen size bedbrbr-One lower-level bedroom with two single bedsbrbrbrbrWe have two full bathrooms—one upstairs with tub and shower combo and one downstairs with a shower. brbrbrbrEverything you need for a great stay is included—toiletries, linens, towels, hairdryer, iron and ironing board, washing machines, detergent, and more!brbrbrbrThere’s plenty more to get excited about!brbr-Hot tub on the patiobrbr-Gas fireplace for cozy firesbrbr-Private deck outside with propane grillbrbr-Walkable to nearby Goose Pondbrbr-Acres of woods to explorebrbr-Smart TV with streaming capabilities in the spacious game roombrbr-Mini-split AC system in most rooms to keep the whole house cool this summerbrbr-Hardwood floors throughout with some area rugbrbr-Two steps to the front door and one one to enter the house through the foyerbrbr-Bring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbrTHE INTERNETbrbr150+ MBPS internet is available throughout the house so you can work, stream your favorite shows, and stay connected during your Berkshires escape.brbrbrbrTHE HOT TUBbrbrRelax and let your worries melt away in our hot tub! We clean and maintain the hot tub regularly, so all you need to bring is a bathing suit.brbrbrbrPlease keep in mind:brbr-The booking guest must be at least 25 years old and must remain present at the property for the entire duration of the stay.brbrbrbrThe Neighborhood:brbrABOUT THE AREAbrbrLee is a charming and picturesque New England town nestled in the heart of the Berkshires. Stockbridge, Great Barrington, and many more lovely towns are all a short ride away. We provide a guestbook with plenty of recommendations on what to see, what to do, and where to dine in the area.brbrbrbrYEAR-ROUND ACTIVITIESbrbrSummer—Grilling, concerts, local attractions, and nearby Goose PondbrbrAutumn—Leaf peeping, fire pit s'mores, and plenty of hiking nearbybrbrWinter—Skiing, snowshoeing, cozy time by the fireplace, and hot tub soaks under the starsbrbrSpring—Family time indoors, hiking, biking, and exploring nearby townsbrbrbrbrOther Things to Note:brbrWe look forward to welcoming you soon! brbrStandard rules like no smoking, no partying, and being respectful of the neighbors apply.brbrBring your furry friends, two dogs are allowed. $50 per dog per stay. Dogs must be at least one year old, sorry no puppies!brbrbrbr-You must agree to the hot tub disclosure after booking for us to have it ready for you. brbrbrbrNo sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.brbr*Damage caused to the hot tub or by pets is not covered by the accidental damage waiver.

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Rent a place that suits your needs

Private vacation home

View 31 Private vacation home

Most popular vacation rentals in Lee

Exceptional(7)

$275.89

/ Nightly

Hotel

Great Place - 2 BD - Kitchen and Pool 

Lee, Massachusetts, United States

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Bath

Sleeps

Exceptional(7)

$457.38

/ Nightly

Condo

Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!

Lee, Massachusetts, United States

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Exceptional(7)

$415.49

/ Nightly

Apartment

Updated and inviting home in Lenoxdale

Lee, Massachusetts, United States

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Exceptional(7)

$412.17

/ Nightly

Hotel

Two Spacious Villas | Indoor Pools, Game Nights & Nature Trails – All-in Escape

Lee, Massachusetts, United States

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Exceptional(7)

$412.17

/ Nightly

Hotel

Two 2BR Villas l From Sauna to Sports Courts – Comfort & Fun for Everyone

Lee, Massachusetts, United States

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Bath

Sleeps

Exceptional(7)

$378.66

/ Nightly

Private vacation home

4BR Home w/ Yard & BBQ, 5 min walk to downtown Lee

Lee, Massachusetts, United States

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Sleeps

Exceptional(7)

$363.03

/ Nightly

Apartment

1500 sqft private entrance with beautiful views of the Berkshire Mountains

Lee, Massachusetts, United States

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Exceptional(7)

$298.08

/ Nightly

Private vacation home

Lovely Lakefront Cottage, Peaceful Setting, Hiking And More

Lee, Massachusetts, United States

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Exceptional(7)

$278.16

/ Nightly

Apartment

Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee

Lee, Massachusetts, United States

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Exceptional(7)

$233.45

/ Nightly

Apartment

Gateway to the Berkshires - Renovated downtown apartment

Lee, Massachusetts, United States

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Vacation Rentals By Owner In Lee, MA

$266.3

$240.16

$994.13

$350.43

$473.65

$892.05

$261.38

$413.25

$204.44

$204.44

$204.44

$525.5

Rent a place that suits your needs

Most popular vacation rentals in Lee

$275.89

$457.38

$415.49

$412.17

$412.17

$378.66

$363.03

$298.08

$278.16

$233.45

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