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.

Holiday Homes in Charlemont

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
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
    Location
    Any Distance
    from
    Price
    per night
    $245 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 23 Rentals in Charlemont
    Sort by:
    Default
    Unique People & Pet-Welcoming Country Haven1 / 37
    (163)Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Travellers' Choice
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 25 kilometres of Charlemont.
    Lake House in Berkshires1 / 21
    (1)Excellent
    North Adams
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    North Adams
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Apartment walking distance to Mass MoCa!!1 / 22
    (2)Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    Reviewed 7 July 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
    See all reviews
    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 10
    Make Enquiry
    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
    Make Enquiry
    Flight's End-A Country Home with Babbling Brook1 / 22
    (9)Very good
    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
    • Cable/satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 December 2017
    We needed a much needed break from the hustle and bustle of the city and we found the perfect place. Flight’s End was secluded, had a lot of empty space for our four legged...
    Reviewed 27 August 2017
    We booked Flight's End for our recent mini vacation and were extremely pleased. The house is definitely a place where people lived and grew old, and had a comfortable...
    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
    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
    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2014
    I stayed in this house with a group of about 14 friends from college (we're a few years out) the weekend after Christmas, and we had a great time staying at Susan's place in...
    Reviewed 3 July 2012
    The home was so perfect. Just a short walk to the center of Shelburne Falls, 5 minute drive to rafting outfitters, swimming holes.Huge house with a great kitchen, but you'll...
    See all reviews
    About this property
    Our 7 bedroom, 3 bath, redone Federal House is the perfect place for family celebrations, school reunions, wellness, writing, quilting or other special interest gatherings. Your whole group can share our dining area and even enjoy the services of a gourmet chef should you desire. We have 8 quiet...
    View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
    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
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    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
    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
    • Cable/satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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 • 24 Park like acres - woods and streams • Perfect location to attend Marlboro Music Festival • Close to Brattleboro (10 miles) located in the Village of West Halifax • House has 4 bedrooms - 2 master bedrooms with Queen Beds • 2...
    View all property information
    Location Information
    West Halifax, Vermont 05358
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Save time - get the best Charlemont rentals sent straight to your email!
    Get the List
    Retreat in the Woods1 / 6
    (6)Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    My husband and I vacationed in the Berkshires to hike and visit the MA state parks. This home is conveniently located within a 30 min. drive to many state parks and hiking...
    Reviewed 20 July 2017
    Lovely home - the pictures don't fully do it justice! The house is shielded from the road and set in a small clearing, so it gets plenty of light and a pleasant breeze at night...
    See all reviews
    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and...
    View all property information
    Location Information
    Savoy, Berkshires 01256
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Jacksonville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Cable/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
    Lakefront Summer Vacation Cottages1 / 5
    (2)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Waterfront
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    A perfect start to our 3 week stay in Mass. Fantastic, quiet, lakeside location with warm water - so different from the UK! Full use of kayaks, canoe, paddleboard and raft...
    Reviewed 22 June 2017
    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
    Whitingham, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Central Heating
    • Grill
    • Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discounts and seasonal specials may be available - call Evolve at *******-1013 for more info! James Gandolfini Stayed Here! Mount Snow Farm is a 120-acre former dairy farm and secluded haven nestled in the Green Mountains near Whitingham, Vermont. The top of this property sits at 2,300' above sea...
    View all property information
    Location Information
    Whitingham, Vermont 05361
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Air Conditioning
    • Patio
    • Grill
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    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
    Adams
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Manor is an elegant home built in the 1800's with a beautiful story and rich history. It offers amazing architecture and style with modern conveniences. Once encompassed within its walls guests will feel its unique small town warmth which adds significantly to its charm. Located in...
    View all property information
    Location Information
    Adams, Berkshires 01220
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    North Adams
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We are located across from Windsor Lake, a nature preserve with a large spring fed pond, swimming beach, and hiking trails. Walk to town. All eco friendly non-toxic paints inside and out, cleaned with natural products only, except occasional use of bleach. Newly renovated kitchen with quartz...
    View all property information
    Location Information
    North Adams, Berkshires 01247
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
    Make Enquiry
    Hawley
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pudding Hollow sits nestled into the woods at a corner of our private drive. This cozy cottage with both deck and screen porch looks out over a grassy lawn and wooded hillside. The fully-equipped kitchen and family room with wood stove run across the front of the house, while the bedrooms and bath...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 5
    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
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious cabin by the brook was originally a two-room log cabin, built in 1935. Over the years a bedroom addition was built on each end, making it a comfortable retreat for up to six people. Located at the end of a dirt road at the edge of the forest and close to the brook, Alice’s Cabin...
    View all property information
    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Valley View1 / 8
    (2)Excellent
    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
    Reviewed 1 week ago
    Singing Brook farm is off of Route 2, and close to Shelburne Falls, MA in the Berkshires. The farm is family owned and everyone is friendly, and helpful. Groceries and other...
    Reviewed 2 weeks ago
    We had the pleasure of staying at Valley View for a long weekend. The house is small but has an open floor plan with beautiful view of a sweeping meadow. We enjoyed watching...
    See all reviews
    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
    Clarksburg
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    • Housekeeping Included
    • Mountain Views
    • Internet Access
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our family home is close to museums (less than 2 miles to MoCA), state parks, hiking trails, skiing cultural events and colleges (Williams, MCLA). Enjoy the beauty of the Berkshires in the comfort of a large farm house with views of Mt Greylock. The 1st floor guest bedroom offers a queen bed with a...
    View all property information
    Location Information
    Clarksburg, Berkshires 01247
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Shelburne Falls
    Studio, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • DVD Player
    • Mountain Views
    • Hot Tub
    • Washer
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags for a peaceful nature retreat at this charming vacation rental studio cabin! Ideally situated on 65 expansive acres, this Shelburne escape offers accommodations for 6 and upgraded amenities such as a floor-to-ceiling fieldstone fireplace and stainless steel appliances. Whether you're...
    View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    Condo/Apartment - 1 Bathroom, Sleeps 6
    Make Enquiry
    List your property
    Owner log in