
Vacation home rentals in Western Massachusetts
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Top-rated vacation home rentals in Western Massachusetts
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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!

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

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.

Once in a Lifetime Hudson River Views
Perfect for reunions, retreats, and celebrations. We designed Riverhouse so you can relax, recover, and get inspired. Gather in one of many common areas or chill in your own room with a view. Watch birds fly, fish jump and trains and ships go by. Chill in the hot tub, build a fire (and finally hang with your teenager), fly a kite , catch fish off a private dock. Morning coffee or sunset cocktails on the deck. Play pool, pingpong, or piano into the night. Drum circle and a dance party? YES!

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

Cozy Glens Falls home 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 the front or back porch or near the fire pit and enjoy the Adirondack air.

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 Lake
Welcome to Lake Congamond's North Pond! Wake up every day just steps from the water. Grill out on the brand new Trex deck with stunning water views, and dock your boats for the duration of your stay. This home features ample parking, central air, cornhole boards, an outdoor dartboard, and a propane-fueled fire pit. The location is great as the house is just minutes away from Bars, Restaurants, and Golf Courses. This vacation rental truly has it all! Book your stay today!

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!

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.

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.

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.
Popular amenities for Western Massachusetts vacation home rentals
Family-friendly vacation home rentals

Luxurious 4 BR Condo at Windham Mountain Resort

Windham castle with a view & minutes to skiing

Serene 4-bdrm lake house

The Dahlia Villa within Westerhall Gardens

Near Ragged Mountain & Sunapee!

NEW. Stylish & clean 2bed duplex 5 min to slopes.

*Farmhouse Chic with Mountain and Lake Views*
Vacation home rentals with a patio

Mountain escape in Hunter/Tannersville

Saratoga Lakefront Belmont Travers 12 min to track

Chez Moo - Hot Tub with a View

Charming Vacation House w/ Pool & HotTub

Beautiful 4bedroom home overlooking Saratoga lake.

Peaceful 3-Bed/3-Bath in Private Lake Community

The Loft - Discount Rates ‼️ Lake George.

Secluded hilltop getaway |Spacious & Cozy |Hot Tub
Vacation home rentals with a washer and dryer

Beautiful 2 bedroom home with panoramic view

Cozy Cabin in a Rural Setting #16

Spofford lake 1 bedroom apartment with boat dock

Tranquility awaits on Amston Lake!

Sunapee Barn Retreat

Berkshire Getaway Vacation rental

Sunny oasis in the woods in Otis

Ludlow Big Family Fun Home
Destinations to explore
- Plainview Vacation rentals
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- Rentals with a fireplace Western Massachusetts
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- Waterfront rentals Western Massachusetts
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- Rentals with a fire pit Western Massachusetts
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- Ski-in/ski-out rentals Western Massachusetts
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- Vacation home rentals Massachusetts
- Vacation home rentals United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Catamount Mountain Ski Resort
- Bushnell Park
- Brimfield State Forest
- Taconic State Park
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Wintonbury Hills Golf Course
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Dinosaur State Park
- Hartford Golf Club
- Talcott Mountain State Park
- Beartown State Forest
- Butternut Ski Area and Tubing Center
- Mohawk Mountain Ski Area
- Mount Tom State Reservation




