House vacation rentals in Pittsfield

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Top-rated house rentals in Pittsfield

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Guest favorite

Home in Athens

4.94 out of 5 average rating, 114 reviews

Private lakefront home, hot tub & resort amenities

Stylish, and private Catskills lake-front house, w/ amazing lake views, a private hot tub, fire pit, beach and dock; community swimming pools, tennis, pickle ball, basketball courts, baseball fields, playgrounds, dog beach & parks, golf driving range. This home has all you need to entertain, and work from. Located 2hrs from NYC, 15-30 minutes from Catskill, Hudson, Woodstock, Hunter and Windham ski resorts, the best restaurants, hiking trails, art galleries, antique shops, and cultural centers.

Guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 106 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 Southwick

4.96 out of 5 average rating, 202 reviews

Linny's Updated Lakeview Cottage - Cozy & Modern

Linny's Lakeview Cottage is updated - with beautiful hardwood floors. - kitchen is finished in white shaker cabinets, granite counter tops & new appliances. - counter joins the kitchen/living room & comfortably sits 6. We will also provide an online guidebook (a few days before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay. Easily access nearby attractions like the Big E, Six Flags, Basketball Hall of Fame, Bright Nights, and more.

Guest favorite

Home in Athens

4.93 out of 5 average rating, 114 reviews

Lake house, 700 ft waterfront - from every room

Panoramic views from the wrap-around deck offers privacy and 700 feet of lake frontage from this comfortable home. Enjoy the sunrise and sunsets views of the lake from EVERY room. Two kayaks, canoe, paddle board to be enjoyed from its private beach. The great room has full lake view, heated floors and two large decks. This home offers 4 bedrooms, 2 and 1/2 baths, a finished lower level that features game room with private deck, ping pong table, giant Jenga, home gym, and large 55in TV.

Guest favorite

Home in Becket

4.87 out of 5 average rating, 323 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 Saugerties

4.9 out of 5 average rating, 113 reviews

Charm and lots of space in a peaceful village

Our beloved house is located in a hamlet one mile north of Saugerties near the Hudson River. Its five bedrooms can comfortably house 9 guests, and dogs are welcome. It has a Large kitchen, very spacious living and dining rooms, a wood stove usable as a fireplace , excellent Wifi ( up to 400 mbps), AC and central heating. Our huge back porch opens on a one acre garden. All this within walking distance to the HITS championships and a 30 minutes drive to the ski slopes of Hunter.

Guest favorite

Home in Athens

4.83 out of 5 average rating, 169 reviews

A Victorian "Lady"

Enjoy an old-fashioned vacation right across the street from the Hudson river. Watch the tides, boats, and barges pass by. Dining, kayaking within walking. Historic Hudson, Olana just 10 min. drive. This is a house to relax, use as a base for other activities. It is not intended as a place to party.. It is a quiet neighborhood. I expect my guests to respect that. There is a weekend special. If you book friday/saturday or saturday/sunday the price is $350.00 for the 2 nights. Thanks

Guest favorite

Home in Sheffield

4.9 out of 5 average rating, 113 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Rental #1 has 2 bedrooms, a FULLY EQUIPPED KITCHEN and it is SUPERCLEAN! (ALSO SEE THE 1 BEDROOM LISTING #2!) Fully renovated, large garden, private entrance, terrace and parking space. Two Queen size beds. High Speed WiFi. Berkshire Blend coffee/decaf, teas, milk, sugar and juice are a first morning welcome gift. Bathroom has radiant floor heat, towel warmer, plush bathrobes, hairdryer and toiletries. We are in the heart of the Berkshires come visit!

Guest favorite

Home in Averill Park

4.98 out of 5 average rating, 170 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 Pine Plains

4.98 out of 5 average rating, 120 reviews

Twin Island Lake House • Hot Tub

Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with private bathroom. Open concept kitchen/living room. A perfect getaway to relax and recharge in our year round 6 person hot tub. Amazing views and sunsets over the lake and mountains. Great hiking, fishing, kayaking, canoeing and bird watching. 16 miles to the center of Rhinebeck. Explore the local farms, restaurants, distilleries and wineries.

Guest favorite

Home in Otis

4.97 out of 5 average rating, 104 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.