House vacation rentals in Brattleboro

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Top-rated house rentals in Brattleboro

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Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 105 reviews

Berkshire Pontoosuc Lake- Modern and Updated

Lakefront Home for Rent. This home has been 100% remodelled! With a beautiful spot directly on Pontoosuc, the new kitchen, bathrooms, fireplace, and glass enclosed family room all benefit from the idyllic scenery. The home has 5 bedrooms and a convertible playroom with a futon for even more space. 2 bedrooms have bunk beds plus a full size bed in them. 2 bedrooms have king size beds and 1 has a queen. The master suite has an en-suite bathroom and a balcony overlooking the lake. Many upgrades!

Guest favorite

Home in Old Chatham

4.95 out of 5 average rating, 21 reviews

Post and Beam Hilltop Sanctuary

Enjoy the quiet countryside/mountain views from this breathtaking private hilltop getaway. Step into our stunning vaulted Post & Beam home with central fireplace, cozy loft and spacious open floor plan that features a full wall of windows/doors to the back wrap around deck that allows for an incredible indoor/outdoor living experience with friends and family. Take advantage of our fully stocked chefs kitchen, comfy beds complete with fresh linens/towels and each bedroom has its own full bath.

Guest favorite

Home in Cambridge

5 out of 5 average rating, 112 reviews

Winding Trails Lake House, Hedges Lake, NY

Beautiful, remodeled lake house w/ private dock and 75 feet of private shoreline! Literally steps from the crystal clear, spring fed waters of Hedges Lake with spectacular views from virtually every window in the house! Cozy living room, fast WiFi, TV's w/ ROKU, central heat & AC, fully equipped kitchen, all new mattresses, bed #1 Master Suite w/ Cal King, full bath & retreat; bed #2 Queen; bed #3 2 adult length twinXL; laundry room, office/work area, covered & open patio areas with gas grill.

Guest favorite

Home in Mount Holly

4.93 out of 5 average rating, 107 reviews

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

Guest favorite

Home in Becket

4.87 out of 5 average rating, 321 reviews

Real Estate:Therapy - Lake, Laundry, Love it

This is what happens when a realtor and an expressive-therapist make a vacation home. You get a decent property, in a good location with little things to help you de-stress, have fun and connect with friends and family. 18 minutes from downtown Lee, in the private Sherwood Forest Community with lake access, laundry, and a level-2 EV charger, this 1500 sq. ft home built in 1987 rejuvenates. We hope you will leave here a little more relaxed, recharged or maybe even a little bit happier.

Guest favorite

Home in Newport

4.97 out of 5 average rating, 32 reviews

Stylish and unique 6 Bedroom in-town property

Charming 100+ year old 3 bedroom house with retro kitchen, spacious, comfortable living and dining rooms is joined with a modern 3 bedroom open concept home with a beautiful kitchen and spacious dining area. Private, peaceful outdoor area includes a grill, firepit, and dining options. Great property for a larger group and/or family reunions. Located a short walk to the village green and assorted shops and restaurants, it is a 10 minute drive to Lake Sunapee Beach and Mount Sunapee.

Guest favorite

Home in Lenox Dale

4.95 out of 5 average rating, 21 reviews

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Enjoy all the Berkshires has to offer from this charming 3BR/2BA home-base in Lenox. Drive 5 minutes to downtown Lenox & 8 minutes to Tanglewood. Go for a hike at nearby October Mountain, Pleasant Valley or Tyringham Cobble. Kick off your shoes and relax on the deck after a fun day out! The neighborhood is quiet & pleasant area to walk. Welcome to your perfect Berkshires getaway home! Great home for short- or long-term stay. Please ask about discounts. Pets are case-by-case.

Guest favorite

Home in Canaan

4.99 out of 5 average rating, 83 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

This newly updated Berkshire lake house with private in-ground pool, is the perfect place for a year-round vacation. Nestled within a small lakefront community where being on the lake is a pass-time in winter, spring, summer or fall. 6 light-filled bedrooms can accommodate a family retreat or 3 families. Enjoy the pool table, chefs kitchen, two living room areas, and wood burning fireplace inside and fire pit outside. All bedrooms and common areas have air conditioning.

Guest favorite

Home in Harrisville

4.9 out of 5 average rating, 10 reviews

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Guest favorite

Home in Averill Park

4.98 out of 5 average rating, 169 reviews

Lake House in Averill Park, NY (age 30+ excl kids)

Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Age requirement of at least 30 years old for guests (except kids).

Guest favorite

Home in Otis

4.92 out of 5 average rating, 146 reviews

The Pinnacle House at Otis Ridge Ski Area!

Otis is the best town for a visit to the Berkshires. It is close to all the places you would want to visit like Jacob's Pillow, Tanglewood, Norman Rockwell Museum to start with. It is also close to hiking trails, swimming, shopping and great restaurants. This wonderful three plus bedroom home is located on the backside of Otis Ridge Ski Area. Wake up and take a walk on the ridge or just sit outside and have your morning beverage with the woods surrounding you.

Guest favorite

Home in Great Barrington

5 out of 5 average rating, 5 reviews

Winter Holiday & Ski Season Rental!

Charming, cozy cottage, walking distance to Lake Mansfield and Main Street attractions, 20 minutes to Tanglewood, 15 minutes to area summer camps or the Zipline at Catamount Ski Area. Freshly renovated throughout, fully-equipped kitchen, large yard with screened dining porch. Comfortable and stylish home in a centrally-located spot. Attention to all the little details.