Holiday Homes in Western Massachusetts

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Top-rated Holiday Homes in Western Massachusetts

Guests agree: These holiday homes are highly rated for location, cleanliness and more.

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Guest favourite

Holiday home in Hudson

4.95 out of 5 average rating, 43 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!

Guest favourite

Holiday home in Albany

4.92 out of 5 average rating, 164 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.

Guest favourite

Holiday home in Ulster Park

4.92 out of 5 average rating, 39 reviews

Weeping Willow Hideaway on the Lake Studio Suite

Private Studio Suite on Mirror Lake. TRAVELING NURSES WELCOME Book 2 nights or more receive complementary wine or soft drink. Take it easy at this unique and tranquil getaway for relaxing Entire suite with lake access Yard is shared with your hosts. Large windows for view of beautiful lake or sit on patio or lakeside for morning coffee. Covered picnic area to have a lakeside picnic Our No pet policy is firm due to allergies so please don’t ask Reiki Master on premises Garage parking in winter

Guest favourite

Holiday home in Monroe

4.93 out of 5 average rating, 46 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 favourite

Holiday home in Warren

4.98 out of 5 average rating, 177 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

Guest favourite

Holiday home in New Paltz

5 out of 5 average rating, 50 reviews

☆Mulberry Guest House☆Private☆Walk to village

The Mulberry Guesthouse is a garden apartment with a romantic living room fireplace, cozy den, sunroom, and two bedrooms -- all fully furnished and equipped for easy living while you’re in town. Private outdoor space includes dining table, propane grill, and fire pit. The beauty of our location is the quiet, wooded setting that feels away-from-it-all, but is also walkable to the cafes, shops, and restaurants of downtown New Paltz. Local walking and biking trails are just 2 blocks away.

Guest favourite

Holiday 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.

Guest favourite

Holiday home in Becket

4.96 out of 5 average rating, 55 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!

Guest favourite

Holiday home in Salt Point

4.93 out of 5 average rating, 74 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 favourite

Holiday home in Williamstown

4.98 out of 5 average rating, 106 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.

Guest favourite

Holiday home in Pittsfield

4.86 out of 5 average rating, 28 reviews

Explore the Berkshires from this charming home.

The whole group will enjoy easy access to everything from this centrally located place. Ski Bousquet, Butternut, or Jiminy Peak. Visit charming towns of Great Barrington, Lee, Stockbridge, Lenox, Adams, N. Adams and Williamsburg. All within a short drive. Soak up some culture by visiting Clark Museum, Mass Moca, or the Rockwell Museum, or listen to some great live music at Tanglewood during the summers.

Superhost

Holiday home in Woodbury

4.86 out of 5 average rating, 28 reviews

UNIQUE and GORGEOUS historic loft style rental

Beautifully bright third floor loft style space with private entry available for your enjoyment. Basic kitchen, laundry, and bath are located on the second floor. Due to the stairs in this unique space, it would be ideal for a single traveler or couple looking for a getaway. Walkable to historic Woodbury, minutes to amazing land trust hiking trails in Roxbury, and only 1.5 hours from NY City.