
Holiday home rentals in Western Massachusetts
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Top-rated holiday 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

Home in Great Barrington. Steps from downtown!
Central and Private! Just steps away from historic downtown Great Barrington. East Mt. 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. 🫶 {STAND ALONE UNIT} Recent review*^ Bed- Not Broken. House- Very Clean.

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

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.

Large elegant 2BR in Village walk to restaurants!
Welcome to the first-floor unit at the historic 1827 House where you can escape to beautiful VT!! Enjoy the spacious great room, King Bedroom, full kitchen, & laundry. Pet Friendly! Close to everything in the Village. Walk on sidewalks to fine restaurants, pubs, wine tasting, weddings, escape rooms, Free Moover shuttle & trails right from the house. Convenient to hospitals in Brattleboro, Greenfield, and Bennington for traveling medical professionals with monthly rates.

Winterberry Lodge: Newly Renovated at Jiminy Peak
NEWLY RENOVATED - 3 BR 2 BA~ sleeps 10, swimming pool, private deck w/ awning, Weber grill Multi-level 3 bedroom house only 2 miles from Jiminy Peak (has community pool). Fully equipped RENOVATED kitchen, fully renovated bathrooms, new floors and carpeting, has "perfect hill" right off the deck to sled and a Weber grill for warmer weather. Cozy loft area to enjoy board games and several smart TVs throughout . Wonderful base to enjoy the Berkshires year around!

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.

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!

Saratoga Springs Rental
Includes entire 3rd fl of an office building: 2 apartments and a large, covered patio(During the winter months 12/1-4/1 the Patio is closed) . Apt 1 includes 2-bedrooms(Queen Beds) each with en suite bathrooms, with an additional half bath. Apt 2 includes one bedroom(Queen Bed) and bathroom. Both apartments include kitchen, living, laundry areas and parking. Located 3.5 miles to the track and 2.9 miles to downtown.

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.
Popular amenities for holiday home rentals in Western Massachusetts
Family-friendly holiday home rentals

Beautiful 2 bedroom home with panoramic view

2 blocks from Warren with an office and Patio db

Once in a Lifetime Hudson River Views

Perfect Serene Waterfront All Season Retreat!

Great top fl near cnter with sunroom and a view cc

Private new house on 10 acres of pristine nature

Lakefront Retreat | Kayaks, Paddle Board & Hot tub

Home in Great Barrington. Steps from downtown!
Holiday home rentals with a patio

Kingswood 4 BR 4 Bath House

Stunning Hudson Valley estate with river front

The Lake

Spacious & relaxing 4Br w deck pool/outdoor shwr

Weeping Willow Hideaway on the Lake Studio Suite

Mount Snow Cozy Condo

Beautiful 4bedroom home overlooking Saratoga lake.

Spacious Urban APT w/4BR & Office in Albany
Holiday home rentals with a washing machine and dryer

Cozy Cabin in a Rural Setting #16

Spofford lake 1 bedroom apartment with boat dock

Berkshires Modern Cabin with Babbling Brook

Lux Boutique Large Private LOFT Pratt St Hartford

Berkshire Getaway Vacation rental

Sunny oasis in the woods in Otis

Furnished Private Studio Prime Location Pratt St

Family Home in the mountains. Get out and explore!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Tiny house rentals Western Massachusetts
- Loft rentals Western Massachusetts
- Farm stay rentals Western Massachusetts
- Flat rentals Western Massachusetts
- Townhouse rentals Western Massachusetts
- Luxury rentals Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Waterfront rentals Western Massachusetts
- Cottage rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Rentals with pools Western Massachusetts
- Chalet rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
- Rentals with a firepit Western Massachusetts
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- Ski-in/ski-out rentals Western Massachusetts
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- Apartment rentals Western Massachusetts
- Boutique hotels Western Massachusetts
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- Rentals with outdoor seating Western Massachusetts
- House rentals Western Massachusetts
- Rentals with beach access Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Rentals with a fireplace Western Massachusetts
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- Holiday home rentals Massachusetts
- Holiday home rentals United States
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Butternut Ski Area and Tubing Center
- Bash Bish Falls State Park
- Kent Falls State Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- June Farms
- University of Connecticut
- Norman Rockwell Museum
- Naumkeag
- Berkshire Botanical Garden
- Hancock Shaker Village
- New York State Museum
- Mount Holyoke College
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- Crooked Lake
- The Egg
- Things to do Western Massachusetts
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