We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Charlemont Holiday Homes

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $265 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Charlemont area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 16 Rentals in Charlemont
    Sort by:
    Default
    Unique People & Pet-Welcoming Country Haven1 / 37
    (156)Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Certificate of Excellence
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometres of Charlemont.
    Retreat in the Woods1 / 6
    (4)Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Charming Affordable  Home for groups up to 141 / 11
    (9)Excellent
    Shelburne Falls
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    PARADISE on EARTH! - Historic 4BR Farmhouse1 / 7
    (1)Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2015
    We rented this house to be close to Mount Snow so our boys could spend their vacation snowboarding. The house was as beautiful as described. The rooms were charming and...
    See all reviews
    About this property
    • 19th Century Farmhouse with beautiful mature gardens<BR>• 24 Park like acres - woods and streams <BR>• Perfect location to attend Marlboro Music Festival<BR>• Close to Brattleboro (10 miles) located in the Village of West Halifax <BR>• House has 4 bedrooms - 2 master bedrooms with Queen Beds...
    View all property information
    Location Information
    West Halifax, Vermont 05358
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Flight's End-A Country Home with Babbling Brook1 / 22
    (6)Excellent
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2015
    Very pleasant place to stay. Felt like staying at Grandma's house in the country. The owner is a very pleasant and easy going fellow and the price is reasonable.House and...
    Reviewed 12 September 2014
    The house was very clean and cozy. Everything was as shown in the pictures. As my friends and I are from the city, we love how quiet the area is. BBQ grill and bonfire were...
    See all reviews
    About this property
    3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Berkshire house w/ fireplace, A/C, WiFi & laundry1 / 27
    (16)Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Housekeeping Included
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2014
    The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
    Reviewed 30 May 2014
    We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
    See all reviews
    About this property
    Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country...
    View all property information
    Location Information
    Plainfield, Hampshire County 01070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Conway
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study "nook", private bath with laundry facilities and a separate entrance. Guests are greeted every morning by two friendly...
    View all property information
    Location Information
    Conway, Massachusetts 01341
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Porch
    • Patio
    • Grill
    • Satellite TV
    • Parking
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck with a patio set and grill, a...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 8
    Make Enquiry
    Jacksonville, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful spacious 3200/sf. log home situated on ten acres very close to Mount Snow Resort. Private and secluded, this property features a wonderful outdoor fire-pit, babbling brook, many hiking, ATV and snowmobile trails. Quaint country living at its finest. Year-round weekly rentals...
    View all property information
    Location Information
    Jacksonville, Vermont 05342
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    Test Listing - Do Not Rent1 / 4
    (2)Very good
    Hawley
    1 Bedroom, 50 Bathrooms, Sleeps 50 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    What an experience-great expanse inside with lots of room to explore. All of our guests enjoyed the plethora of bathrooms the place had to offer. Minus one star for only having...
    Reviewed 4 weeks ago
    It is a pretend cave, but it is a nice pretend cave. I have never stayed in a cave with so many bathrooms. The best part is the location, though - there is a gold course o site...
    See all reviews
    About this property
    Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 1 Bedroom, 50 Bathrooms, Sleeps 50
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Jacksonville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Satellite TV
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a relaxing escape to this three-bedroom Jacksonville cabin, a lakefront home with a private deck, lovely lily pond views, and a wonderful location close to outdoor adventures in every season. This three-level home sits atop a small hill on the eastern shores of Gates Pond, where you'll enjoy...
    View all property information
    Location Information
    Jacksonville, Vermont 05342
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Very nice and quiet, clean and confortable. Kids enjoy Adults love it and i will say we will go back
    See all reviews
    About this property
    We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique and enjoyable! The property is...
    View all property information
    Location Information
    Goshen, Hampshire County 01032
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Plainfield
    7 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Apartment/Flat, in Plainfield at Perry's, from 232 USD per night per person and 233 USD for 2! Discover Plainfield, and enjoy the advantages of staying at a locals': practical advice, a welcoming atmosphere and great prices. A Whole Lodging (for cottage, appartment, house), from 1 to 10 people. At...
    View all property information
    Location Information
    Plainfield, Hampshire County 01070
    Condo/Apartment - 7 Bedrooms, 1 Bathroom, Sleeps 10
    Make Enquiry
    Greenfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Terrace
    • Housekeeping Included
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brandt House is a three-and-a-half-acre, turn-of-the-century estate located in a charming residential area of Greenfield, just minutes from I-91 and Route 2 in northwestern Massachusetts. Walking distance to downtown Greenfield and in the northern Pioneer Valley where culture, history, adventure,...
    View all property information
    Location Information
    Greenfield, Massachusetts 01301
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Whitingham, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Outdoor Dining Area
    • Parking
    • Satellite TV
    • Washer
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discounts and seasonal specials may be available - call Evolve at 877 818-1013 for more info! Please go to youtube and search "JohnsFarmDrone+Music1" to view aerial footage of the property! Mount Snow Farm is a secluded haven nestled in the Green Mountains near Whitingham, Vermont. This rustic,...
    View all property information
    Location Information
    Whitingham, Vermont 05361
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Hawley
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Central Heating
    • Parking
    • Private Garden
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Valley View is a charming one-bedroom house looking out over a large meadow from the top of a hill. The house features a wraparound deck which extends the living space into the outdoors, and large picture windows and sliding glass doors bring light and views inside. A woodstove in the living room...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Make Enquiry
    List your property
    Owner log in