Vacation home rentals in Western Massachusetts

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Top-rated vacation home rentals in Western Massachusetts

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Guest favorite
The exterior of a three-story townhouse showcases a welcoming porch with a railing and multiple seating areas. Beautiful greenery surrounds the property, accentuating the wooden structure. A staircase leads to the upper level, while two planters with greenery add a touch of nature to the entrance.
Vacation home in Hudson
4.92 out of 5 average rating, 64 reviews

La Maison Hudson: Charming 1BR In Prime Location

Welcome to La Maison in Hudson! This charming three-story townhouse, just two blocks from vibrant Warren Street, is perfect for families, friends, or a romantic getaway. Apartment 2 offers 1 bedroom, 1 bath, and accommodates 2 guests. Enjoy cozy thrifted decor, a private balcony, convenient parking, and a fully equipped kitchen with a dining table for six. Warren St: 3-min walk Train station: 15-min walk Olana: 8-min drive Art OMI: 15-min drive Your ideal mix of convenience & culture awaits!

Superhost
Vacation home in Athens
4.87 out of 5 average rating, 118 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard.  You will enjoy:  • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

Top guest favorite
An elegantly set dining table displays black plates, clear glassware, and cloth napkins. A lit candle adds a soft glow, while a modern kitchen is visible in the background, featuring stainless steel appliances and a cozy living area with seating.
Vacation home in Warren
4.98 out of 5 average rating, 211 reviews

Private new house on 10 acres of pristine nature

Brand new home! Bring friends and family to this private and stylish place. House provides everything you need for a comfortable and peaceful stay. Fully equipped kitchen, inviting living spaces, large front and back yards with many exploring trails and a pond a few steps away from the house. Close to many 5 star restaurants, wineries, galleries and shops. Hiking, swimming, boating, skiing just to mention a few outdoor activities Close by: Kent School Mohawk Ski Area Lake Waramug High Watch

Top guest favorite
Vacation home in Glens Falls
4.99 out of 5 average rating, 80 reviews

Glens Falls house near Lake George & Saratoga

Use our cozy 3 bedroom home away from home to enjoy everything in the Lake George area. We are 5 minutes to downtown Glens Falls restaurants, 10 minutes to West Mountain, 15 minutes to Lake George, and 20 minutes to Saratoga. Feel at home during any season visiting family or friends, as a home base for work, vacation, skiing, or to just get away to enjoy living and a small town feel. Relax with a coffee on one of the porches, a bbq, or a peaceful walk around the neighborhood or downtown.

Top guest favorite
A modern kitchen is highlighted by a large island with a quartz countertop and seating. Natural light fills the space through broad windows, offering views of the surrounding greenery. Professional-grade appliances are provided, creating an inviting area for culinary activities.
Vacation home in Windham
4.91 out of 5 average rating, 117 reviews

*Farmhouse Chic with Mountain and Lake Views*

Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

Guest favorite
A modern kitchen area is showcased with a wooden countertop and sleek cabinetry. Two wooden stools are placed at the counter. A cozy seating area is visible in the background, featuring a dark sofa with patterned cushions. Natural light streams in through large windows.
Vacation home in Hudson
4.85 out of 5 average rating, 150 reviews

Great top fl near cnter with sunroom and a view cc

Experience comfort and convenience in this Hudson apartment, perfect for solo travelers, couples, or small families. Enjoy the cozy ambiance of this space, complete with a fully equipped kitchen, and organic washing and cleaning products. You'll find comfortable sleeping arrangements, as well as Smart TV and board/card games for your entertainment. Unwind on your private patio. Whether you're here for business or leisure, don't miss out on this spacious, bright, peaceful space.

Top guest favorite
A serene garden setting is depicted with a vibrant carpet of fallen red leaves covering the ground. A wooden bench is positioned under a majestic tree, surrounded by lush greenery and rocks, creating a peaceful atmosphere for outdoor relaxation.
Vacation home in Holmes
5 out of 5 average rating, 24 reviews

The Dahlia Villa within Westerhall Gardens

Reconnect with nature at this unforgettable escape. A gorgeous mature garden in a park like setting. Two queen bedrooms, great room, 75 inch TV. Radiant bathroom floor. Outdoor 45,000 gallon salt pool…that’s shared with other property (summer months - POOL IS FOR REGISTERED GUESTS ONLY - NO EXCEPTIONS) Decompress in our sauna. This a no smoking/vaping property. A sprawling 17plus acre estate. Dahlia Villa is a beautiful two bedroom completely independent unit on the estate.

Guest favorite
The image captures a serene lakefront view, showcasing lush greenery surrounding a secluded house. A wooden dock extends into the calm water, providing access to the lake, while the sunlit landscape emphasizes the tranquility of the natural setting.
Vacation home in Becket
4.97 out of 5 average rating, 61 reviews

Perfect Serene Waterfront All Season Retreat!

Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two wooded acres of forested land. Explore the stream that runs through the property, or just sit on the large deck or down by the crystal clear lake and listen to the sounds of nature while feeling the warm sun on your face. Very private--just one near neighbor. The sunny house has 2 bedrooms, study with sofa bed, 2 full baths, full kitchen!

Superhost
A lovely exterior view of the house features a spacious deck adorned with light-colored seating and a dining area, surrounded by greenery. The sloped metal roof complements the white siding, creating a modern yet quaint appearance. Large windows allow for natural light to fill the interior.
Vacation home in Salt Point
4.91 out of 5 average rating, 90 reviews

Riverfront rustic farmhouse near Rhinebeck

This historic Clinton Hollow house was built by Isaac Fraleigh in the late 1700's and overlooks the waterfalls of Wappingers Creek. The house has the architectural details of an antique colonial and the open, spacious feel of a modern contemporary. The great room with its big fireplace has different vibes and seating areas and is just perfect for family and friends gathering. The Petanque field in the garden add a fun convivial activity.

Guest favorite
The exterior of the barn-style home is framed by vibrant autumn foliage, with a spacious yard covered in fallen leaves. Large windows and a front porch create an inviting facade, while the cupola adds a distinct architectural feature to the roofline.
Vacation home in Sunapee
4.98 out of 5 average rating, 50 reviews

Serene Sunapee Barn

Bring family and friends to this serene Lake Sunapee destination. Year-round fun and adventure at your doorstep. Our 4-bed, 3-bath barn restoration has it all. Minutes to the mountain, Dewey Beach, and Sunapee Harbor. Expansive first floor gathering space with modern amenities. Beach passes included, store and launch your boat locally. Comfortably sleeps 9, with bedrooms on both floors. Come enjoy all that Sunapee has to offer!

Guest favorite
An open, airy space features a wooden staircase leading to the upper level. A small dining area includes a table and two stools, while a comfortable seating area is visible in the background. Natural light filters through large windows, illuminating the modern design.
Vacation home in Great Barrington
4.94 out of 5 average rating, 273 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington. East Mountain Hiking trails are a quick walk away. Enjoy sunset views with friends and family, before you walk into town for a night out! Butternut Ski Area: 5-10 min drive(traffic depending) Tanglewood: 20-25 min This new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple. 🫶

Guest favorite
The spacious great room features large windows that provide natural light and views of the lake. A leather sectional sofa occupies the center, complemented by rustic accent chairs. A ceiling fan hangs above, and an area rug adds warmth to the wooden floor.
Vacation home in Hadley
5 out of 5 average rating, 24 reviews

Entire House-Sacandaga Lakeview Home on Rosebloom

Beautiful Sacandaga lakeview home! A space created for guests who appreciate a calming aesthetic to retreat, rejuvenate and relax! Spacious first floor great room overlooking Sacandaga lake with mountain views! Enjoy lake and access across the street from the property. Many great interior features including 3 fireplaces, modern bathrooms, custom kitchen with large island, bar and two levels of outdoor deck/patio spaces!

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