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Vacation home rentals in Western Massachusetts

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in Western Massachusetts

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

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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

4.93 out of 5 average rating, 45 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!

The living room features a large sectional sofa with a plush texture, complemented by a soft area rug. Two mirrors and a modern light fixture add style to the neutral walls, while sheer curtains allow natural light to filter gently into the space.

Vacation home in Albany

4.92 out of 5 average rating, 171 reviews

Spacious Urban APT w/4BR & Office in Albany

Visiting Albany for work, vacation, or to visit family? The Twitchell Estate is a spacious 4BR home that will be perfect for your stay. This elegantly designed Boho Chic rental comes with amenities such as self-check-in, Netflix, Disney+, Apple TV, and many other streaming options if you're looking to relax indoors, and a private laptop-friendly office with Wi-Fi if you need to get work done. Enjoy free coffee and tea in the stocked kitchen, with everything you need to feel like you are at home.

A two-story green house is set against a backdrop of rolling hills, with trees and a barn visible in the surroundings. Sunlight creates a warm glow on the mountains, while a landscaped yard features greenery in front of the home.

Vacation home in Monroe

4.94 out of 5 average rating, 48 reviews

Family Home in the mountains. Get out and explore!

Old-fashioned charm awaits at our comfortable, well-equipped base for your next family adventure. Attractions from art galleries to zip-lining are a short drive away - including hiking, mountain biking, white water rafting, and fly fishing. Mass MoCA, the Clark Institute, Berkshire East, and Mount Snow are nearby. At night, adults can linger over dinner while the kids watch a movie - out of the way - upstairs! We can't wait to welcome your families to share an authentic rustic experience.

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, 185 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

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

4.92 out of 5 average rating, 100 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, you'll be in proximity to the best of the Catskills: skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Amenities includes business Wifi, gourmet kitchen, washer/dryer, deck w/ bbq grill, outdoor fire pit, badminton, and more.

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, 239 reviews

Home in Great Barrington. Steps from downtown!

First Things First… Let’s Keep the Love Alive! ❤️ 🙌 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. 🫶

The exterior of The Country Inn is shown, featuring a covered entrance with a sloped roof and decorative columns. Lush greenery and flowering shrubs frame the front, while the building's muted tones complement the natural surroundings. Nearby parking spaces are visible under an overcast sky.

Vacation home in Hancock

4.96 out of 5 average rating, 26 reviews

Ski in/Ski Out - Building 1 Condo at Jiminy Peak

Book today and spend your ski days only steps from the lift! Get first tracks or even night ski from this one bedroom condo in Building 1 at The Country Inn at Jiminy Peak. Private parking, kitchenette, and all of the comforts of home. Visit any season to explore this beautiful Berkshire mountain. Enjoy private, gated parking, walk to the country store to get essentials, and even rent equipment right at the mountain. A family-friendly condo with food options for all.

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, 59 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!

An open kitchen and dining area feature natural wood floors and high ceilings. The kitchen is equipped with modern appliances and a large island. Windows allow ample natural light, illuminating the dining table and additional seating areas. Exposed wooden beams add a rustic touch.

Vacation home in Salt Point

4.93 out of 5 average rating, 76 reviews

Riverfront, cozy 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.

Top guest favorite

A garden scene is presented with a wrought-iron chair nestled among frosted pink and green sedum flowers. A leafless tree stands in the background, framed by autumn foliage. Rolling hills are visible beyond the landscaped area, hinting at the surrounding natural beauty.

Vacation home in Williamstown

4.98 out of 5 average rating, 109 reviews

ALL welcome: Lovely 1 BR studio, Berkshires beauty

Come as you are - we welcome ALL visitors. Relax and soak in your surroundings in this new 1 bedroom vacation spot. Part of a barn conversion, the space is clean and bright and ideally located for those exploring all the Berkshires has to offer. Perfect for an individual or couple looking to escape to a serene and beautiful setting - a stream abuts the property and hiking/snowshoeing trails are accessible out the front door.

Top guest favorite

A spacious great room features a wooden dining table with multiple chairs, surrounded by light-colored walls. Two chandeliers provide illumination, while a large seating area with a white sofa rests near a decorative fireplace. Windows dressed in sheer curtains allow natural light to fill the room.

Vacation home in Dover

5 out of 5 average rating, 48 reviews

Large elegant 2BR in Village walk to restaurants!

This is the first-floor unit at the historic 1827 House where you can escape to beautiful VT!! Enjoy the spacious great room, full kitchen, & laundry. Pet Friendly! Close to everything in the Village. Walk on sidewalks to fine restaurants, pubs, wine tasting, weddings, antiques, escape rooms, Free Moover shuttle & trails right from the house. Fun Oyster Shucking Class with Wine pairing next door Columbus Day WKD!

Top guest favorite

A small enclosed garden area features a wooden table and chairs surrounded by greenery. A barbecue grill is positioned on one side, while sliding glass doors provide access to the interior. The space is enclosed by wooden privacy fencing, enhancing the tranquil atmosphere.

Vacation home in Beacon

5 out of 5 average rating, 83 reviews

Private, modern carriage house. Great for couples.

Newly built in 2022, our charming, modern carriage house is tucked away within a small courtyard garden on a quiet residential street in the heart of Beacon NY. Guests will enjoy an efficient, elegantly designed and furnished interior with views of the Mount Beacon ridgeline from this comfy and private abode. The owners are long-time Airbnb hosts who work hard to ensure their guests have a peaceful, relaxing stay.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Western Massachusetts vacation home rentals

Free parking on premises

Air conditioning

Family-friendly vacation home rentals

The exterior of Tamarack House is framed by colorful autumn foliage, with a welcoming sign positioned by the gravel driveway. The home features a split-level design, visible balcony, and landscaped surroundings that blend into the natural setting.

Vacation home in Grantham

4.93 out of 5 average rating, 55 reviews

Relax&Play @ Tamarack House- Golf, Ski, Lake, Hike

A wooden staircase descends through a snowy landscape toward a cozy A-frame cabin, illuminated warmly from within. Dense trees surround the cabin, and a small shed is visible in the background. Soft lighting creates a serene evening atmosphere.

Private room in Lanesville

Hunter Mountain Ski House Rental

A cozy living area features a large sectional sofa adorned with decorative pillows. A minimalist coffee table is positioned in front, while a gentle light illuminates the corner from a floor lamp. Natural light filters through the window, enhancing the calming atmosphere.

Vacation home in Newport

4.95 out of 5 average rating, 129 reviews

Walk to The Heart of All That is Newport

Top guest favorite

The lakefront property features a two-story building with large windows, surrounded by lush greenery. Dock space for two boats is accessible from the shoreline, with a spacious lawn area leading to the water, providing ample opportunity for outdoor activities.

Vacation home in Tilton

5 out of 5 average rating, 64 reviews

Cheerful 4 bedroom, lake-front vacation home

Top guest favorite

A bright living area features a comfortable light-colored sofa set against a textured brick wall. Two patterned armchairs and a coffee table create a cozy seating arrangement, while large windows and skylights flood the space with natural light. A striped rug adds a nautical touch.

Vacation home in Newport

4.98 out of 5 average rating, 58 reviews

Newport Condo with Harbor View and Rooftop Deck!

A comfortable living area is displayed with a spacious sectional sofa adorned with decorative cushions. A round coffee table occupies the center, with a collection of books visible. Large windows provide abundant natural light and offer views of the surrounding landscape. A wall-mounted television and built-in shelves are also present.

Vacation home in Windham

Luxurious 4 BR Condo at Windham Mountain Resort

A modern kitchen is highlighted by a spacious island with four black bar stools. Light-colored cabinets contrast with a dark backsplash, while stainless steel appliances are present. Natural light fills the room through multiple windows, enhancing the inviting open layout.

Vacation home in Narragansett

4.88 out of 5 average rating, 32 reviews

NEW! Reel vacation 3min to Scarborough Beach

A traditional two-story home is presented, featuring a light-colored exterior with blue shutters. A welcoming entryway is positioned under a small roof. Lush greenery surrounds the property, including well-maintained shrubs and trees that provide shade, contributing to a pleasant outdoor environment.

Vacation home in South Kingstown

4.78 out of 5 average rating, 27 reviews

Charming 5 Bedroom Home In Downtown Wakefield

Vacation home rentals with a patio

An open-concept kitchen and dining area features natural wood accents and large windows that allow natural light. The kitchen is equipped with modern appliances, while the dining area includes a long wooden table paired with black chairs. A cozy seating area with a couch is visible.

Vacation home in Tannersville

4.96 out of 5 average rating, 23 reviews

Mountain escape in Hunter/Tannersville

Vacation home in Wappingers Falls

4.97 out of 5 average rating, 59 reviews

Once in a Lifetime Hudson River Views

Top guest favorite

The exterior of a cozy three-bedroom home features light-colored siding and classic black shutters. An American flag is displayed on the porch, which is accessible by a small set of steps. The well-kept lawn enhances the welcoming appearance of the property.

Vacation home in Glens Falls

4.99 out of 5 average rating, 74 reviews

Cozy Glens Falls home near Lake George & Saratoga

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, 23 reviews

The Dahlia Villa within Westerhall Gardens

A serene in-ground pool is surrounded by lush greenery and landscaped areas. Sun loungers and wooden seating are positioned near the water's edge. Two umbrellas provide shade for relaxation, adding to the inviting outdoor space under a clear blue sky.

Vacation home in Highland

5 out of 5 average rating, 36 reviews

Charming Vacation House w/ Pool & HotTub

The open-concept living room and kitchen feature warm wooden ceilings and natural light. A large dining table and kitchen island are surrounded by sleek chairs. A comfortable seating area includes decorative elements and plants, while an electric fireplace adds a cozy focal point.

Vacation home in Lake George

4.94 out of 5 average rating, 68 reviews

The Loft - Discount Rates ‼️ Lake George.

Aerial view of a spacious house surrounded by trees, featuring a heated pool with four chaise lounges positioned nearby. A barbecue area and outdoor seating are visible on the deck, alongside a small shed. Solar panels are installed on the rooftop.

Vacation home in Kingston

4.94 out of 5 average rating, 78 reviews

Secluded hilltop getaway | heated pool + hot tub

A spacious living area is highlighted by large glass doors that open to a deck, allowing natural light to fill the room. A dark sofa with decorative pillows is centered on a soft rug, while a modern coffee table adds functionality. A glimpse of the outdoor seating can be seen in the background.

Vacation home in Carmel Hamlet

4.85 out of 5 average rating, 61 reviews

Serene 4-bdrm lake house

Vacation home rentals with a washer and dryer

A modern living room features a dark leather sofa facing a mounted television. A sleek fireplace with a stone finish is positioned against one wall. The open layout leads to a kitchenette visible in the background, designed with white cabinetry and contemporary appliances.

Vacation home in Temple

4.79 out of 5 average rating, 57 reviews

Cozy Cabin in a Rural Setting #16

A calm beach scene captures gentle waves lapping at the shore, with a sandy expanse leading to a peaceful ocean. In the background, a series of homes are nestled atop a green, coastal hill, offering a serene view of the landscape.

Vacation home in Narragansett

4.83 out of 5 average rating, 18 reviews

37 Algonquin Trail Narragansett-Seaside

Two white Adirondack chairs are set beside a small white table on a stone patio, facing the calm, reflective surface of Spofford Lake. Lush greenery and flowers frame the serene view of the lake and distant hills under a partly cloudy sky.

Vacation home in Chesterfield

5 out of 5 average rating, 22 reviews

Spofford lake 1 bedroom apartment with boat dock

A view from the covered porch showcases calm waters with gentle ripples. The distant shore features a slight incline with green grass. A railing frames the scene, providing a clear perspective of the serene landscape against a bright blue sky.

Vacation home in Ballston Spa

Saratoga Lakefront Belmont Travers 12 min to track

A hallway connects various spaces, featuring a long dining table with dark chairs. A decorative chandelier hangs above, and a cozy living area is visible at the end. A green plant adds a touch of nature, while a TV is positioned along a light wall.

Vacation home in Pittsfield

4.86 out of 5 average rating, 28 reviews

Explore the Berkshires from this charming home.

A serene lakeside view showcases a grassy area with four bright blue Adirondack chairs arranged around a stone fire pit. The tranquil waters of Shellcamp Pond reflect a colorful sunset, framed by lush trees and a wooden dock extending into the lake.

Vacation home in Gilmanton

4.96 out of 5 average rating, 99 reviews

Lakefront Retreat Boat Dock Amazing Views

An aerial view captures the lakefront vacation house surrounded by greenery and calm waters. The property features a spacious lawn leading to the lake, with several vehicles parked near the house, highlighting its accessibility and serene location in the lake community.

Vacation home in Athens

4.87 out of 5 average rating, 111 reviews

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

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, 47 reviews

Sunapee Barn Retreat

Destinations to explore