
Vacation home rentals in Western Massachusetts
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Top-rated vacation home rentals in Western Massachusetts
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Family-friendly vacation home rentals

Chalet on the Hill
We had a lovely stay at Chalet on a Hill and Nadine was lovely to work with. House is very private with great views and close drive to Windham where dinner was recommended. The grocery store nearby has everything you need if you want to make the house feel like home for the weekend. We will certainly look to book again.

Ludlow Big Family Fun Home
Kelly was super responsive. The house was 5 minutes away from Okemo.

2 blocks to Warren ST w/ a yard and parking
Excellent location, close to all the art galleries, cafes and restaurants Hudson has to offer. It is also a short drive to other points of interest like Olana, the Thomas Cole house and Catskill, NY.

Great top fl near cnter with sunroom and a view cc
The space was clean, cozy, and exactly as advertised! We had no trouble getting in, and Vladimir was very responsive and flexible about our check-in time. We were easily able to walk to the center of town and to the Amtrak station, and all of the best restaurants in Hudson are nearby.

2 blocks to Warren ST with an office and a yard cb
Booked the place for a guest visiting. They loved the place. Was clean and spacious. Would rent again.
Vacation home rentals with a patio

Okemo Oasis - 6 Bedrooms, 3.5 Baths, 2 Kitchens
The Okemo Oasis home was a fantastic place for our annual cousins’ ski trip. It had plenty of space for everyone to sleep, relax, and enjoy the open living, dining, and kitchen area. The many bathrooms was a big plus, and check-in was seamless. There were very few downsides—the beds weren’t the most comfortable but were manageable for a short stay, and the road access was a bit tricky, though that’s beyond the host’s control. While there was no cellular service, they had WiFi. Overall, it’s a great home, and we would definitely stay here again!

La Maison Hudson: Charming 1BR In Prime Location
We absolutely loved our stay! It was so close to town, but very peaceful and quiet at night. The home had everything we could need, and was a perfect spot to relax in between exploring Hudson. Highly recommended!

Once in a Lifetime Hudson River Views
A true retreat spot- peaceful with lots to do. The home is a perfect Air BnB- lots of bedrooms, great hang out spaces, fun amenities (pool table, ping pong, hot tub, huge tv), awesome kitchen. The topper is the amazing river setting! One of the best spots I have stayed. Highly recommend!

Country oasis on 75 acres with pond and hiking
A beautifully remodeled country home in an amazing location; with a view of Shwangunk Mountains and the Hudson valley, surrounded by large open fields, providing privacy and perfect for stargazing. The home is spacious, comfortable, tastefully furnished, perfect for a party of 6 to even 8 people. The kitchen has all the best equipments, tools. The "on demand" hot water system worked very well for us. Shane is a wonderful host, very responsive and helpful. There are amazing hiking trails close-by or one can just walk around the area and enjoy the outdoors right on the property. We very much hope to come back sometimes in the spring or summer time for some hiking and enjoying what this wonderful home provides with visitors.

Cozy home near Lake George & Saratoga
GREAT HOUSE, GREAT SERVICE.... HOPEFULLY WILL BE BACK

Riverfront, cozy farmhouse near Rhinebeck
The house is so well preserved yet the updates make it feel comfortable and modern. The fireplace was awesome to share with our family on a cold and rainy night. Being close to the waterfall/river was also lovely. We were there between seasons, and in the summer it must be divine.

Secluded hilltop getaway | heated pool + hot tub
This is our third time staying at Mark and Anne’s house and we are already looking forward to coming back! Mark and Anne are INCREDIBLY responsive and very helpful. This is the perfect place for a get to gather with friends or family. The house is stunning and has everything you need - perfectly private location as well! Thank you Mark & Anne!

UNIQUE and GORGEOUS historic loft style rental
Jamie is a fantastic host! She is also kind-hearted and very hospitable. For example, Jamie asked me to let her know if I would be arriving after dark during check-in in order to leave the lights on for me and she checked in with me during this longer stay to see how everything was going, offering me recommendations for restaurants in the area or nearby hiking spots. If you get the opportunity to stay at her beautiful home I highly recommend it! Thank you Jamie!
Vacation home rentals with a washer and dryer

Beautiful 2 bedroom home with panoramic view
I have stayed at this home many times and it never disappoints . All ways very clean and check in and out very easy . I would definitely recommend this home .

Cozy Cabin in a Rural Setting #16
The cabin was clean, cosy & comfortable and a good location to have my pets.

Perfect Serene Waterfront All Season Retreat!
Quiet neighborhood. House and property are welcoming and just as described. We had a snowstorm check-in day and Larry was responsive and made sure the snow and ice were cleared prior to our arrival. The kids and the dog enjoyed exploring the property despite the single digit temps and 20 inch base of snow. This property is close to so many awesome winter activities! We made the most of our 4 night/5 day stay and went cross country skiing at Canterbury Farm, snow tubing at Bousquet Mountain, and snowboarding at Otis Ridge. It was great to have a well appointed kitchen for home cooked meals, and a woodstove with plenty of firewood to beat the frigid temps. Overall - awesome!

Explore the Berkshires from this charming home.
Lovely place, exactly what my family needed

Lakefront Retreat | Kayaks, Paddle Board & Hot tub
Great space, beautiful lake, host was friendly and responsive, no problem getting an uber to Athens and Hudson. Would absolutely stay here again.

Perfect Windham getaway for year round fun!
Some essentials in place such as toiletries coffee salt etc Home was comfortable and suitable to meet our needs Would definitely return

Large elegant 2BR in Village walk to restaurants!
Big thank you to Rich & Nicky, their place was gorgeous, spacious and comfortable for my parents, sister and our dogs. We felt right at home. They were very responsive and helpful throughout the weekend, a pleasure to communicate with. House was a 5 min drive to Carinthia, 9min drive to Wilmington. We took their recommendation and had my 40th birthday/easter brunch at the Sawmill just across the street, delicious. Went to the Alpenglow Bistro the night before for dinner, we couldn’t be more pleased with the dining options this stay. Was happy to have skied this late in April in southern, VT as well! Would highly recommend staying at the 1827 House when visiting Mount Snow and the surrounding area. High end features like the towel drying racks were an added bonus and the espresso machine was a hit! Will definitely be booking again!

Sunapee Barn Retreat
Entertainers paradise! Kitchen was fully stocked with platters, glasses, place settings, and specialty baking and cooking equipment. Just bring the food and nothing else is needed. Enough space for a kids and adult party on separate floors. Decorate well in minimalist style with all the modern conveniences. Even though there was a surprise snow storm on a holiday, was kept in the loop with plowing. They were very attentive. Thank you! Made many memories.
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- Rentals with beach access Western Massachusetts
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- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Berkshire East Mountain Resort
- Albany Center Gallery
- Six Flags New England
- Taconic State Park
- Bousquet Mountain Ski Area
- Mount Sugarloaf State Reservation
- Mount Snow Ski Resort
- Otis Ridge
- Bash Bish Falls State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Bushnell Park
- Hartford Golf Club
- Rockledge Golf Club
- Kent Falls State Park
- Shuttle Meadow Country Club
- Dinosaur State Park
- Huck Finn’s Playland, Albany
- Canterbury Farm
- Naumkeag
- Stump Sprouts Ski Touring Center
- Berkshire Botanical Garden
- Things to do Western Massachusetts
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