House vacation rentals in Pittsfield

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Top-rated house rentals in Pittsfield

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Pittsfield

4.97 out of 5 average rating, 115 reviews

Berkshire Lake- Modern and Updated-close to skiing

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!

Top guest favorite

Home in Round Top

4.96 out of 5 average rating, 195 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Top guest favorite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Guest favorite

Home in Athens

4.92 out of 5 average rating, 118 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

4.88 out of 5 average rating, 338 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 Sheffield

4.91 out of 5 average rating, 117 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

"238 Main" has two rentals. Only one rental is rented at a time. Rental #1 has 2 bedrooms, FULLY EQUIPPED KITCHEN and is SUPERCLEAN! (SEE THE 1 BEDROOM LISTING #2!) We are conveniently located between Butternut and Catamount ski stations. Fully renovated, large garden, private entrance, terrace and parking space. Queen size beds. High Speed WiFi. 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 Athens

4.84 out of 5 average rating, 170 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 Catskill

4.94 out of 5 average rating, 109 reviews

Catskill Village House close to dining shops

New for winter 2025 outdoor heated igloo. Quiet street with private parking. Large outdoor deck. Close to Hudson, Hunter and Woodstock. Nearby skiing and hiking. Windham and Hunter ski areas. And north lake. Numerous restaurants, breweries cafes in the bustling Village of Catskill. Short walk to Hudson River and two waterfront parks Need more space. Property is adjacent to https://www.airbnb.com/h/studiocatskillvillage https://www.airbnb.com/h/catskillwaterviewhouse

Guest favorite

Home in Pine Plains

4.98 out of 5 average rating, 122 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 area for 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 Averill Park

4.98 out of 5 average rating, 174 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 Albany

4.91 out of 5 average rating, 220 reviews

Modern home, King Bed 4 bed 2bath, Crib, parking

Come relax at a Hidden Gem in the heart of Albany, NY. It is centrally located between Albany Med hospitals and Saint Peters Hospital and in close proximity to the downtown college campuses of UAlbany, Saint Rose, Albany Pharmaceutical, Albany Law school and medical school, and the New York State capital. Some of the best restaurants and pubs are just minutes from this central location. It is only a 15-minute ride to the Albany International Airport.

Guest favorite

Home in Palenville

4.96 out of 5 average rating, 162 reviews

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a family-and-pet-friendly yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

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What guests are saying

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

5 out of 5 average rating, 10 reviews1 month ago

There is not a shortage of things to do at Anthony's place. The game tables, sauna and hot tub made the weekend really fun, especially for the non skiers of the group. The view from the house is also spectacular! We would definitely rent this place again.

Home in Wilmington

What guests are saying

Private lakefront home, hot tub & resort amenities

4.95 out of 5 average rating, 132 reviews5 days ago

We had a fantastic stay! Our group of 8 adults, 1 toddler, and 2 dogs had an amazing time. The house was spacious, clean, and comfortable—perfect for a family getaway. Vincent was an incredible host—attentive, thoughtful, and quick to respond to anything we needed. He even had small trash bags delivered when we asked, and followed up when the delivery had an issue to make sure it was corrected. One of the highlights was the binder he provided, which was full of helpful information about the house and local area—it really helped us plan our stay. The kitchen was another standout: impressively stocked with basics like flour, sugar, and salt, plus a KitchenAid mixer, toaster, coffee maker, food storage containers, multiple cutting boards, and lots of serving ware. It made cooking for our large group so easy. We felt truly taken care of the entire time. Vincent’s hospitality made all the difference. We’d absolutely love to stay here again!

Home in Athens

What guests are saying

Modern Glass House

4.75 out of 5 average rating, 60 reviews6 months ago

This was our second time staying in this special house. Waking up in the cozy bed and feeling like you are sleeping in the beautiful woods with deer just outside the giant expansive windows is really something. The property and surroundings are gorgeous, private and serene. The house itself is perfect for our family. The bedding and linens are quality. The space is charming and magical.

Home in Hudson

What guests are saying

Sun Filled Lenox Retreat - Minutes to Tanglewood!

4.96 out of 5 average rating, 27 reviews2 months ago

This is one of our favorite Airbnb properties. This was our second visit and everything was great. Great amenities, great location, and great communication. We ended up being there during a lot of snow and difficult weather and Bespoke management took great care of things. We love the area, close to restaurants and skiing. Looking forward to visiting again.

Home in Lenox Dale

What guests are saying

Modern 4 season lakefront rental

5 out of 5 average rating, 20 reviews6 months ago

An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!

Home in Athens

What guests are saying

Summer & Leaf Season Rental!

5 out of 5 average rating, 6 reviews3 months ago

What a lovely home! It’s in the residential neighborhood above Great Barrington, which means it’s walkable to Lake Mansfield and the trails there and also either a short drive or a nice walk to everything downtown GB has to offer. The house is squeaky clean with nice kitchen amenities, a yard, and a beautiful detached screen porch for warmer months. Perfect size for a small family and very cozy. We will be back!

Home in Great Barrington

What guests are saying

Lakefront cottage on burden lake in Averill park

4.89 out of 5 average rating, 9 reviews5 months ago

Very peaceful! Space was comfortable and it was nice to have a relaxing getaway and take a step back from work. Can’t wait to book again in the summer and take full advantage of what the lake has to offer! Lauren was an excellent host and very communicative.

Home in Averill Park

What guests are saying

Berkshire Lake House, gunite pool, Chef's Kitchen

4.99 out of 5 average rating, 86 reviews2 months ago

Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!

Home in Canaan

What guests are saying

Walking distance to Lifts. Avoid Parking Fees!

5 out of 5 average rating, 12 reviews1 month ago

We really enjoyed our stay at Emilio’s. It was perfect for our friend group of 14. The bunny hill is just across the street, so you can take the magic carpet up and then ski over to the Carinthia lift. It was very easy to get to the mountain. The house seemed newly renovated. There was plenty of parking. We had a wonderful time!

Home in Dover

What guests are saying

Post and Beam Hilltop Sanctuary

4.96 out of 5 average rating, 25 reviews3 months ago

We really enjoyed our stay at Sandi’s place. Each bedroom has its own bathroom, which is great for couples and families. The kitchen had everything we needed to cook a big NYE dinner. And it was just a few mins from Chatham center and I90, while still quiet and isolated. Sandi was great at communicating with us and was very flexible about check in and check out times, which we appreciated. We had one toddler with us and there was also a pack and play and a high chair. We would stay here again!

Home in Old Chatham