Vacation rentals in Blandford

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Top-rated vacation rentals in Blandford

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Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 437 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Top guest favourite

Home in Becket

4.99 out of 5 average rating, 73 reviews

Hot Tub, Canoe, Hike, Dog Friendly, Berkshires!

Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Patio w/ Hot tub, fire pit -Acre wooded/secluded lot -8 Private beaches (NOT beach front) -Private Canoe -Appalachian Trail hiking -Wineries/Breweries -Master w/Queen. -2nd bed with 1 Twin/Full Bunk -Full size pull out couch - Kitchen w/utensils, pans, appliances, condiments. -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Generator on site

Top guest favourite

Treehouse in Tyringham

4.99 out of 5 average rating, 317 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Guest favourite

Guesthouse in Lenox

4.9 out of 5 average rating, 276 reviews

The Coach House | Modern 2BR Loft + Views & Pool

Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Top guest favourite

Farm stay in Blandford

5 out of 5 average rating, 46 reviews

Freeland Brook Farm - stunning Berkshires view

Escape from it all at this modern 1840s farmhouse on a working farm in the Berkshire hills of Western Massachusetts. Featuring chef's kitchen, soaker tub, and panoramic views, it is the perfect New England getaway for any season. Enjoy birdwatching (we have around twenty birdhouses), stargazing, and leaf peeping. Nice hikes less than 10 minutes away. 20-45 minutes from Berkshires attractions like Jacobs Pillow, Tanglewood, and the Norman Rockwell Museum. Check out our guide for activities!

Guest favourite

Cottage in Becket

4.94 out of 5 average rating, 238 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit (access via uneven steps) • Canoe & 2 kayaks • Smart TV & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Guest favourite

Home in Blandford

4.85 out of 5 average rating, 81 reviews

Relaxing Home nestled in Rural Hilltown

Beautiful Modern Home with large yard nestled next door to The Berkshires. Enjoy a coffee in the sunroom or deck. There is a large yard, fire pit and kayak access. Alexa enabled in most rooms. A three minute walk to the Blandford Country Store, Breakfast Bistro, and Watson Park. Within 15- 30 minutes of dining, shopping, hiking trails and ski trails. Otis Ridge Ski Area is 15 mins, Tanglewood is 40 mins, Jacobs Pillow 22 mins, Lee Premium Outlets 30 mins, MGM Casino 35 mins.

Guest favourite

Home in Lee

4.99 out of 5 average rating, 289 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

Top guest favourite

Cabin in Otis

5 out of 5 average rating, 13 reviews

Berkshires Lakefront Boho Modern Retreat

Welcome to Watson Pond Lodge in the Berkshires. This beautiful lakefront contemporary home, with architecture that intentionally focuses on the peaceful lake view, has been designed for your comfort and relaxation. Explore the Berkshires year round and see what the area has to offer: from skiing in the winter, to Tanglewood and Jacob’s Pillow in the summer and leaf peeping in the fall. Or just enjoy the tranquility of our lakefront lodge for a rejuvenating weekend away.

Top guest favourite

Apartment in Otis

4.96 out of 5 average rating, 118 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 292 reviews

Berkshires Cottage by Lake. Year Round Adventures.

THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX(will consider pets.)(90 second walk through wooded path to lake)

Top guest favourite

Home in Otis

4.95 out of 5 average rating, 165 reviews

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.