Lee Rentals
- From $570 per night (USD)
VRBO
Upscale Architecturally Designed Berkshire Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy all the Berkshires has to offer in this Historic South Lee home. Perched on a hillside just across the road from t ...
From $570 per night (USD)VRBO
- From $252 per night (USD)
VRBO
Stockbridge Vacation by Norman Rockwell
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This 1900 farmhouse in the village of Stockbridge offers all the convenience of walking to restaurants, shops, the Red L ...
From $252 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Garfield Townhouse in the Berkshires on Main St
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Townhouse on Main St in Lee at Garfield House in the entrance to the Bershires. Easy walk to all of Main St Resta ...
From $175 per night (USD)VRBO
- From $455 per night (USD)
Expedia
The Freckled Hen's Berkshire Nest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My home is a sweet, cozy, private, and very clean farmhouse style Cape in the safe, very quiet and sweet neighborhood of ...
From $455 per night (USD)Expedia
- From $437 per night (USD)
VRBO
Sun Filled Lenox Retreat-Minutes to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home-base in Lenox. Drive 5 minutes to downtown Lenox & ...
From $437 per night (USD)VRBO
- From $499 per night (USD)
VRBO
* Private Berkshire Escape* Monthly Pricing Avail
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Private home offering relaxation with a beautiful property. This cozy home will give you the comfort you need ...
From $499 per night (USD)VRBO
- From $275 per night (USD)
VRBO
Stockbridge Village Cottage With Mountain View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Old meets new in this lovely cottage, a short walk to the Red Lion Inn. Lots of light, comfortable furniture, beautiful, ...
From $275 per night (USD)VRBO
- From $632 per night (USD)
VRBO
The Gatehouse on Golden Hill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: "We are located in the heart of America's cultural epicenter known as the Berkshires. Known as the \""Gatehouse ...
From $632 per night (USD)VRBO
- From $279 per night (USD)
VRBO
Beautiful 2BD Villa in Berkshires Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We're located in the beautiful Berkshire Mountains of western Massachusetts, a regional center for performing and visual ...
From $279 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Lenox, private setting, close to Tanglewood rents by month
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully furnished, well-located Lenox home has a brand new kitchen ! Central Air Conditioning, a King bed in b ...
From $190 per night (USD)VRBO
- From $613 per night (USD)
VRBO
Beautiful Farm House Near Family Ski Mountains And Other Fun Winter Activities
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This gorgeous farmhouse has four bedrooms each with a private full bathroom. Each bedroom has a queen size bed, sitting ...
From $613 per night (USD)VRBO
- From $387 per night (USD)
VRBO
Mountain View Retreat w\/ Hot Tub by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Exceptional VIEWS!! Take in the sunrise sipping coffee on the front porch & the sunset in the evening while relaxing on ...
From $387 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Booking for the 2022 Fall Season. For more photos and information go to our website at www.lenoxmarental.com. Enjoy the ...
From $250 per night (USD)VRBO
- From $246 per night (USD)
VRBO
COZY LOFT w\/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
The LOFT is a unique private large 690 s.f. modern cabin like structure with great forest and garden views and access ...
From $246 per night (USD)VRBO
- From $149 per night (USD)
VRBO
In the Heart of Everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Lee Massachusettes! Located in the heart of the Berkshires, just 15 minutes to Tanglewood, 15 minutes to Jaco ...
From $149 per night (USD)VRBO
- Click For Pricing
Expedia
Charming cottage in Norman Rockwell's Stockbridge with two decks!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Light, sunny, charming 3-4 bedroom cottage built in 1832 in Norman Rockwell's Stockbridge, a five minute walk to the Red ...
Click For PricingExpedia
- Click For Pricing
VRBO
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sited in the original Ice House of the estate and grandly expanded, The Ice House Cottage is a delightful duplex, 2 bedr ...
Click For PricingVRBO
- From $475 per night (USD)
VRBO
Renovated 1860's Farmhouse, across from the Miraval.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ideally located just two minutes from the center of Lenox and across the street from the Miraval Resort and Spa. This e ...
From $475 per night (USD)VRBO
- Click For Pricing
VRBO
One Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Country chic in design, the Old Bath House is decorated in shades of coral, bisque and turquoise. A spacious living room ...
Click For PricingVRBO
- Click For Pricing
Expedia
Two Bedroom Luxury Cottage at Blantyre, Relais & Châteaux
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located down a peaceful path lies a secluded two-bedroom cottage with period American furnishings and modern amenities o ...
Click For PricingExpedia
- From $558 per night (USD)
VRBO
Fox Hollow Luxury Ranch Laurel Lake
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
Awesome Berkshire Location. 1000 feet of Laurel Lake frontage shared with private dock , 2 canoes and 2 kayaks. Large o ...
From $558 per night (USD)VRBO
- Click For Pricing
VRBO
Perfect New England-y Condo Resort, Berkshire
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Holiday Inn Club Vacations Oak n' Spruce Resort is nestled in the beautiful hills of the Berkshire Mountains, putting yo ...
Click For PricingVRBO
- From $643 per night (USD)
VRBO
Stunning Berkshire custom luxury home in private wooded community- walk to lake
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
*******Perfect Home for 1 to 12 People******* 5 BR's with 2 King Beds + 2 Queen Beds + 4 Twin Beds ...
From $643 per night (USD)VRBO
- From $656 per night (USD)
VRBO
5Bdrm\/6Bath estate on Lenox - Stockbridge border, near BSO Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 20
Historic, elegant, recently renovated estate on 7 acres. BBQ grills outdoors. Near Jacob's Pillow Dance Festival, BSO ...
From $656 per night (USD)VRBO
- From $539 per night (USD)
VRBO
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to e ...
From $539 per night (USD)VRBO
- From $325 per night (USD)
VRBO
Spacious Comfortable Charming Family Farmhouse Great Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
ABOUT OUR PROPERTY: Experience a little of old New England. Our VRBO is a charming historic family farmhouse apartment( ...
From $325 per night (USD)VRBO
- Click For Pricing
VRBO
Eight Bedroom Luxury Property at Blantyre, Relais & Châteaux
- Bedrooms:
- 9
- Bathrooms:
- 8
- Sleeps:
- 16
Blantyre, a proud member of Relais & Châteaux, is an award-winning, luxury resort, featuring elegant guest accommodation ...
Click For PricingVRBO
- From $400 per night (USD)
VRBO
Perfect Holiday Retreat, Completely Renovated, Central Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sp ...
From $400 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
This spacious, sunny condo at Foxhollow on the Lenox/Lee border is perfectly situated for you to enjoy the natural beaut ...
From $335 per night (USD)VRBO
- From $497 per night (USD)
VRBO
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Newly Renovated for 2023 Cape Cod Style ,4BR, 4BA, sleeps 10-12. New fully equipped kitchen w/ center island, indoor an ...
From $497 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Beautiful, secluded, private resort in the heart of the Berkshires in Lenox, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A secluded resort nestled in the heart of the Berkshire Mountains, located in a scenic area where there is a wide variet ...
From $250 per night (USD)VRBO
- From $334 per night (USD)
Expedia
Gorgeous, Private, Family-Friendly, Organic Home with a Great Location in Lee
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WIFI SERVICE The current carrier, Spectrum provides broadband internet ...
From $334 per night (USD)Expedia
- From $795 per night (USD)
VRBO
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tangle ...
From $795 per night (USD)VRBO
- From $360 per night (USD)
VRBO
Equipped Villa with Access to Amazing Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy an awesome location and access to a number of exciting amenities including a fitness center, 2 pools, a hot tub, d ...
From $360 per night (USD)VRBO
- From $222 per night (USD)
VRBO
Villa with Access to Various Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
When you stay in our villa, you'll have access to a number of exciting amenities including a fitness center, 2 pools, a ...
From $222 per night (USD)VRBO
- From $283 per night (USD)
VRBO
Spacious Villa with Access to Various Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is the perfect villa for your group! Enjoy an awesome location and access to a number of exciting amenities includi ...
From $283 per night (USD)VRBO
- From $262 per night (USD)
VRBO
Villa with Access to Amazing Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sleeps 4 up to 6 people (Max 5 Adults) - Large and small outdoor pool - Two indoor pools: Open - Hot Tub - 2 on-site B ...
From $262 per night (USD)VRBO
- From $848 per night (USD)
VRBO
Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 6 bath home takes advantage of its prime location on Laurel Lake, offering breathtaking waterfront views ...
From $848 per night (USD)VRBO
- From $323 per night (USD)
VRBO
Centrally Located Historical Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Come to enjoy views from this private, country escape. Decorated with many cool antiques and theatre related ob ...
From $323 per night (USD)VRBO
- From $369 per night (USD)
VRBO
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort ...
From $369 per night (USD)VRBO
- Click For Pricing
VRBO
Berkshire Get away
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Beautiful old home in Lee Massachusetts. Two bedrooms one bath on a quiet street in Lee Massachusetts. A front porch to ...
Click For PricingVRBO
- From $756 per night (USD)
VRBO
Historic Stockbridge Villa on 25 acres sleeps 23
- Bedrooms:
- 7
- Bathrooms:
- 11
- Sleeps:
- 23
At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and ...
From $756 per night (USD)VRBO
- From $259 per night (USD)
VRBO
Berkshires Summer Rental - Lee\/Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Sunny three bedroom condo available for summer rental , with two full baths. Shaded front porch and sunny rear deck wi ...
From $259 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the beautiful Lakeside Condominiums at Fox Hollow in Lenox/Lee, MA. This newly furnished condo is spacious a ...
From $450 per night (USD)VRBO
- Click For Pricing
VRBO
Great house in Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Three bedroom house, one en suite on first floor(can be twin or king), two (both queen) on second floor sharing a bathro ...
Click For PricingVRBO
- From $300 per night (USD)
VRBO
Your Invited to the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Location, privacy & charm! This lovely 3-bedroom, 2.5-bath house has just been newly designed and furnished. Close to d ...
From $300 per night (USD)VRBO
- From $570 per night (USD)
VRBO
Stylish Mid-century Modern Berkshires Cape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard an ...
From $570 per night (USD)VRBO
- From $300 per night (USD)
VRBO
1500 sqft private entrance with beautiful views of the Berkshire Mountains
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come enjoy a quiet getaway in Western Massachusetts. 2 bedrooms, (3 beds, 1 Queen, 1 Double and 1 twin) 1 bath, open ki ...
From $300 per night (USD)VRBO
- Click For Pricing
VRBO
Expansive Berkshires walk to town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Large and elegant house built into a sunny hillside that feels both cozy and expansive. Located in the center of the Be ...
Click For PricingVRBO
- From $558 per night (USD)
Expedia
Lakeview Retreat - mins. to downtown Lenox, Stockbridge, Lee
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 14
Open and bright retreat in beautiful setting with privacy and lake views. Centrally located between Lenox and Stockbridg ...
From $558 per night (USD)Expedia
- From $100 per night (USD)
VRBO
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated unit with fireplace in main room, bathroom, bedroom (queen) and kitchenette.The unit also has a futon th ...
From $100 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Cozy retreat in beautiful country setting
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Nestled at the base of October Mountain, this cozy retreat has all the comforts of home. Sit out on the deck and sip you ...
From $270 per night (USD)Expedia
- Click For Pricing
VRBO
New! Inspired Country Retreat in Lenox Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Looking for a centrally located destination for a ski weekend? Cozy up by the fireplace for at this stylish winter count ...
Click For PricingVRBO
- From $144 per night (USD)
Expedia
2 Bedroom newly renovated townehouse, beautifully decorated at Garfield House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Garfield House Vacation living for short or longer stays in a newly renovated townhouse is in close proximity to all Ber ...
From $144 per night (USD)Expedia
- From $165 per night (USD)
VRBO
2 Bedroom\/2 Bath Vacation Rental in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the tranquility and comfort of a four-season country getaway. This newly renovated luxury vacation rental is house ...
From $165 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Garfield Gallery 2 BR in the Annex
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is an economical and convenient unit that is part of the Garfield Vacation Property Complex on the Main St. in Lee. ...
From $175 per night (USD)VRBO
- From $299 per night (USD)
VRBO
Two Blocks from the Red Lion Inn & next to Berkshire Theater
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - gr ...
From $299 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Elegant 19th Century New England 2BR vacation rental at Garfield House
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This super comfortable and spacious Berkshires getaway is located on Main St. in Lee, Massachusetts. The main level has ...
From $200 per night (USD)Expedia
- From $1169 per night (USD)
VRBO
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
** Check out the Playhouse on the Netflix series The World's Most Amazing Vacation Rentals. It's included in the Gourmet ...
From $1169 per night (USD)VRBO
- From $471 per night (USD)
VRBO
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
This is a completely renovated 5 bedrooms and 3 baths house that is situated on a private street, 5 min drive to either ...
From $471 per night (USD)VRBO
- From $113 per night (USD)
VRBO
Garfield House Studio at 208
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 0
Our new studio is on Main St, Lee , convenient to all of the town's amenities and a part of the Garfield House complex o ...
From $113 per night (USD)VRBO
- Click For Pricing
Expedia
Long term vacation rental. Quiet clean and comfortable all one level
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a all one level, 1st floor, 1bedroom & 1bathroom in a 2 family home. The property has been recently updated with ...
Click For PricingExpedia
- From $152 per night (USD)
VRBO
Summer in the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Spend the SUMMER in the HEART of the BERKSHIRES! Just minutes from both the Lenox and Stockbridge Town Beach with access ...
From $152 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Lovely Lakefront Cottage, Peaceful Setting, Hiking And More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely lakefront cottage has been a favorite family gathering place of ours for 30 years. It sits on picturesque Lo ...
From $286 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Spectacular setting on your own private lake close to it all!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is the perfect Berkshire home to swim, hike, leaf-peep, ski, sled, engage in the cultural attractions of the neighb ...
From $550 per night (USD)VRBO
- From $460 per night (USD)
Expedia
Berkshire Vacation Rentals: Private Access To Laurel Lake, Enjoy Lake Life
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This two story lake home has all the room needed for you and your guests to experience the serenity of lake liv ...
From $460 per night (USD)Expedia
- From $480 per night (USD)
VRBO
Spacious Berkshire Home - Year Round Retreat.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Looking for a spacious house in a secluded neighborhood to spend time with family/friends? Our vacation home has 5 bedro ...
From $480 per night (USD)VRBO
- From $342 per night (USD)
Expedia
Rockspring by AvantStay | Huge Berkshires Estate
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
This charming Berkshires estate consists of a beautiful main house, an ample separate recreation space, and a private po ...
From $342 per night (USD)Expedia
- Click For Pricing
VRBO
Architect Designed Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy all the Berkshires has to offer in this Historic South Lee home. Perched on a hillside just across the road from t ...
Click For PricingVRBO
- From $275 per night (USD)
Expedia
Historic 1817 Berkshire Farmhouse- Close to Everything!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
View our Superhost AirBNB reviews here: https://www.airbnb.com/rooms/26598493? preview_for_ml=true&source_impression_id= ...
From $275 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy Condo with resort amenities
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Resort offers multiple pools, hot tub, sauna, exercise room, locker rooms with showers, wireless internet throughout ...
Click For PricingVRBO
- From $348 per night (USD)
VRBO
Relax between your Berkshire adventures! Easy walk to town! Centrally located!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Owner operated with pride 😊 Our vacation home in Lee Massachusetts is centrally located to ALL THINGS BERKSHIRES! In th ...
From $348 per night (USD)VRBO
- Click For Pricing
VRBO
Family fun @ The Ponds at Foxhollow Resort
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Ponds at Foxhollow is a distinctive residential community in Lenox, MA. The community features elegantly designed ho ...
Click For PricingVRBO
- From $950 per night (USD)
Expedia
Amore Estate - sleeps 12 in beds
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Fully renovated and decor updated in 2024! 8 acre property, shared with one carriage house not rented, with amazing vie ...
From $950 per night (USD)Expedia
- From $125 per night (USD)
VRBO
7 nights in our 1 br, full kitchen villa. Only 110 per night
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Available for the last week of July. 320 beautiful acres at the foot or Beartown State Forest, Oak 'n Spruce offers plen ...
From $125 per night (USD)VRBO
- From $200 per night (USD)
Expedia
The Blue Jay - a New England Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come stay at our cozy Blue Jay Cottage in the Berkshires. Quiet and intimate, it is an idyllic setting for your next rom ...
From $200 per night (USD)Expedia
- From $230 per night (USD)
VRBO
Clean & Modern space with a mix of original warmth and charming renovation.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to "The Hideaway On Main " in Stockbridge Center. Our recently renovated 2 bedroom unit offers a clean mix of ...
From $230 per night (USD)VRBO
- From $215 per night (USD)
Expedia
Charming 3 bed in the HEART of the BERKSHIRES! Walk to town! Ski retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3-bedroom home in the heart of the Berkshires (Lee). Walkable to Big Y Grocery, Main St/center of town (multipl ...
From $215 per night (USD)Expedia
- From $407 per night (USD)
VRBO
Berkshire Retreat- Stone's throw to downtown Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Berkshire Retreat - A stone's throw to downtown Lenox Our calendar is updated in real-time & our nightly rates are accu ...
From $407 per night (USD)VRBO
- From $232 per night (USD)
Expedia
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Country Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $232 per night (USD)Expedia
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VRBO
Large Country farmhouse in the Berkshires.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to Brookside Farm, a 5000sqft one level farmhouse on 70 acres of woodlands and fields with a large pond that yie ...
Click For PricingVRBO
- From $399 per night (USD)
Expedia
Romantic Boutique Hotel \/ B&B - Deluxe Firespa Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our romantic "Firespa" suite with a Jacuzzi for two with a smokey mirrored surround, terry cloth robes and slippers, hea ...
From $399 per night (USD)Expedia
- From $299 per night (USD)
VRBO
Romantic Boutique Hotel \/ Bed and Breakfast - Smallest Room in The Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The smallest room around literally a double bed 2 nightstands and a bathroom, for those traveling light and just need a ...
From $299 per night (USD)VRBO
- From $299 per night (USD)
Expedia
Romantic Boutique Hotel \/ Bed and Breakfast - Standard Queen Handicap Accessible
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A traditional room with great charm, L'Atelier is completely handicapped accessible. This room, with its queen-sized bed ...
From $299 per night (USD)Expedia
- From $349 per night (USD)
VRBO
Romantic Boutique Hotel \/ Bed and Breakfast - Standard King With Gas Fireplace
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
La Chambrette is our economy oriented "Little Chamber," a room as charming as its name. Its private bath with a whirlpoo ...
From $349 per night (USD)VRBO
- From $399 per night (USD)
Expedia
Romantic Boutique Hotel \/ Bed and Breakfast - Deluxe Schoolhouse Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The exquisite Deluxe Schoolhouse Suite provides an impeccable setting for your holiday. Lounge next to the gas-operated ...
From $399 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Romantic Boutique Hotel \/ Bed and Breakfast - SchoolHouse Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The regal king-sized canopy bed and the charming sitting area merge with modern amenities - a gas-operated fireplace, te ...
From $399 per night (USD)VRBO
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VRBO
Fox Hollow Lakeside Condo, Minutes to Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Five bedroom condo on 223 acre manicured estate in the heart of the Berkshires. Laurel Lake views from most rooms and us ...
Click For PricingVRBO
- Click For Pricing
VRBO
Quaint Single Story 1Bd with Vintage Charm, Walk to Downtown Restaurants & Shops
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our charming 1 bedroom, 1 bath single-level duplex, located just 2 town blocks from the heart of downtown Lee ...
Click For PricingVRBO
- From $221 per night (USD)
VRBO
Great Place - 2 BD - Kitchen and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick ...
From $221 per night (USD)VRBO
- From $353 per night (USD)
VRBO
Sun-Filled Lenox Retreat - Minutes to Tanglewood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Enjoy all the Berkshires has to offer from this charming 3BR/2BA home-base in Lenox. Drive 5 minutes to downtown Lenox & ...
From $353 per night (USD)VRBO
- From $218 per night (USD)
VRBO
Great Place - 2 BD - Kitchen - Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures , our Resort in the Berkshires is the perfect New England-y place to unwind and kick ...
From $218 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Fabulous In-town Stockbridge Pied-á-Terre, pet friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Light filled brand new stand alone home steps from quintessential Main Street Stockbridge. Large open great room, 2nd f ...
From $250 per night (USD)VRBO
- From $243 per night (USD)
Expedia
Cozy Berkshires Cottage w\/ 11 Private Acres!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Like something out of a storybook, this idyllic 1-bedroom, 1-bath vacation rental is a hidden gem in the heart of the Be ...
From $243 per night (USD)Expedia
- From $4542 per night (USD)
VRBO
Chambery Inn \/ 7,000 Sqft Luxury Historic Berkshire landmark on Main Street
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 24
***Location, Location, Location!*** The Berkshires is world-renowned for its natural beauty, artistic heritage, and c ...
From $4542 per night (USD)VRBO
- From $237 per night (USD)
VRBO
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Experience the beauty of the Berkshires from Cordelia, your charming Massachusetts home with a chic cottage style and ro ...
From $237 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Berkshire Retreat. Heart of the Berkshires. Walkable to town and hiking trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover 'Berkshire Retreat': A charming New England home, steps from hiking trails, near ski mountains, and walkable to ...
From $475 per night (USD)VRBO
- From $401 per night (USD)
Expedia
Berkshire Manor for Lasting Memories
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our beautiful Berkshire's retreat, a spacious home where families and friends can gather for some quality tim ...
From $401 per night (USD)Expedia
- From $124 per night (USD)
VRBO
Holiday Inn Oak n' Spruce Resort -1BD Sleep up to 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: The Natural Beauty of the Berkshires Vacations in the Berkshires are the stuff of Norman Rockwell paintings. B ...
From $124 per night (USD)VRBO
- From $350 per night (USD)
Expedia
4BR Home w\/ Yard & BBQ, 5 min walk to downtown Lee
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled on an expansive and well-manicured 0.46-acre lot, this pet-friendly, 4-bedroom home presents a tantalizing mix o ...
From $350 per night (USD)Expedia