Family-friendly vacation rentals in Charlemont

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Popular amenities for Charlemont family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Chalet in Wilmington
4.95 out of 5 average rating, 98 reviews

Rustic Sunny Vermont Home near Mount Snow

AndreaRating, 5 stars1 month ago
Couldn't say enough great things about both the hosts and the property. Just lovely home - very spacious, and clean and cosy. The area is gorgeous, with a lot to do. Mt. Snow and Hermitage skiing are very close, and Wilmington and the area are charming. Host was very gracious and kind..thank you!
Top guest favorite
Home in Colrain
4.94 out of 5 average rating, 176 reviews

Secluded Farmhouse Retreat - stunning views

SophonRating, 5 stars1 day ago
This was a great home away from home. Wish it didn’t rain as much as it did. We really wanted to walk the grounds more. Inside was cozy and warm. Anything you needed it was there. Definitely thinking about coming back in the winter because it would be a perfect winter wonderland. Thanks again Sophon
Guest favorite
Farm stay in Valley Falls
4.89 out of 5 average rating, 223 reviews

Country Getaway Lodge / Ranch

TrevorRating, 5 stars3 months ago
Fantastic space for a large group. We had 10 people for a New Year’s Eve ski weekend, and this was the ideal spot for it. Hot tub was a great treat. Be warned - the floors are squeaky, so if you’re a light sleeper in a large group bring ear plugs.
Top guest favorite
Cottage in Shaftsbury
4.99 out of 5 average rating, 683 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

PrasenRating, 5 stars2 weeks ago
Great local restaurant scene. Beautiful location and property.
Superhost
Home in Northampton
4.88 out of 5 average rating, 632 reviews

The Farmhouse - Hot tub eclectic farmhouse 3 br

KatherineRating, 5 stars3 weeks ago
A peaceful location with chill activities for all ages...we enjoyed the phonograph, the retro Atari, the hot tub, the window bird feeder, and watching birds in the spacious yard and conservation area. Herons, hawks, and songbirds viewed. The hot tub was sparkling clean, and the linen robes were a thoughtful touch. Wifi worked great. We arrived late but instructions for entry were crystal clear. Virginia answered my questions promptly and warmly. Definitely a winner.
Top guest favorite
Home in Newfane
4.98 out of 5 average rating, 136 reviews

Peaceful cabin close to skiing & Brattleboro

MarinaRating, 5 stars1 month ago
This house is incredibly comfortable and well equipped. The location is lovely and private. We came for relaxation and with the fire pit and the hot tub we got our money's worth. My friends who are great cooks enjoyed the gas stove and some very well seasoned cast iron pans. Come here and enjoy the natural light and comfy space.
Superhost
Cottage in Becket
4.65 out of 5 average rating, 164 reviews

A Magical Spot on Little Robin Lake

SebastianRating, 5 stars6 months ago
Truly a magical spot--in October, the fall colors. Any time, the lake view, and the absolutely lovely sunroom.
Guest favorite
Home in Dover
4.97 out of 5 average rating, 93 reviews

Wonderful House! Rec Room HotTub Firepit Garden!

KevinRating, 5 stars1 month ago
Celine’s place was great! Plenty of room for our party of 4. We felt right at home with all the amenities at the property. The kitchen was fully stocked with everything you’d need to cook but we opted to go out for dinner during our stay. We’ll def book again when in the area.

Family- and pet-friendly home rentals

Guest favorite
Cabin in Jamaica
4.88 out of 5 average rating, 112 reviews

Cozy Log Cabin near Stratton/Mt. Snow-pet friendly

JamesRating, 5 stars1 month ago
Christina was an excellent host who ALWAYS responded to any of my questions or concerns immediately and courteously. Her space was exactly as described and very spacious as well as a fantastic environment for a group to get together and have a great time! I highly recommend Christina’s place for a great time with a large group, she is the ideal host who works tirelessly to provide an amazing space for her guests!
Top guest favorite
Guesthouse in Stephentown
5 out of 5 average rating, 410 reviews

Dog Friendly Studio

JihanRating, 5 stars1 week ago
This was our sixth visit to Maple Hill Farms — we just can’t get enough of it! Philip truly the best host, and his home is pure magic. We’re so grateful to have met him and to experience his incredible hospitality and a property filled with the most amazing creatures.
Guest favorite
Home in Great Barrington
4.94 out of 5 average rating, 126 reviews

The Hideaway: Berkshire Home - village of Egremont

LeahRating, 5 stars3 months ago
This was the second time staying in this house with another family. Can't beat the convenient location to local mountains for skiing. House is spacious and plenty of room for two families of 4. Shiyrah is friendly and communicative.
Superhost
Farm stay in West Brattleboro
4.94 out of 5 average rating, 132 reviews

Lilac Ridge Farm House

MatthewRating, 5 stars4 months ago
We had a great stay at Lilac Ridge! The house was near and spacious, plenty of room for our family. We stayed in quite a bit and enjoyed the farm (including a visit with the calves!) and the house. The little farm stand had some nice things, including fresh eggs, maple syrup, honey, and soap, all local. Ross and Amanda were super responsive and took care of all our needs. Thanks so much!
Guest favorite
Home in Jamaica
4.81 out of 5 average rating, 405 reviews

1850's VT Farmhouse on the River

MichaelRating, 5 stars6 months ago
We had a great experience with Erin and our stay! Erin was incredibly friendly and welcoming. She made sure to respond promptly to all our questions and requests, which really made us feel at home. Erin went above and beyond to accommodate our needs, ensuring we had everything we required for a comfortable stay. Her genuine care made our experience truly special. If you're looking for a wonderful host and a cozy place to stay, I highly recommend booking with Erin.
Top guest favorite
Apartment in Northampton
4.95 out of 5 average rating, 241 reviews

Cedar Wet Room w Soaking Tub

AlexRating, 5 stars3 months ago
It was very peaceful, great get away from the city. Good for the dogs. The copper tub is amazing, we could not get enough of it. And the dual showers felt so good. It felt very homey. Mr. John was a a great host.
Guest favorite
Tiny home in Jamaica
4.94 out of 5 average rating, 1,256 reviews

Apple Blossom Cottage: A Tiny House

JulieRating, 5 stars5 days ago
We enjoyed our stay at Domenic with 2 kids on school break! The tiny house is just as described, colorful, well organized and very comfortable. We enjoyed making a fire outside on a beautiful spring evening and checking out the peacocks!
Top guest favorite
Home in New Salem
4.89 out of 5 average rating, 215 reviews

Stone n' Sky Lodge

JasonRating, 5 stars5 months ago
I genuinely don't know what to say other than the fact that this may be one of the greatest places I've had the honor to lodge at. I did a lot of vetting across New England to find a wonderful place that could sleep a decent amount of people, provide a scenic and comfortable escape, and keep us entertained. Sarah's wonderful Stone and Sky Lodge exceeded every expectation I just listed. It's cozy, warm, and feels like a hidden nook! The scenery and nature couldn't be more beautiful. I never got the pleasure to meet Sarah, though I wish I did. Over messages and from what my friends told me, I just know that Sarah is the most hospitable and kind host that I've talked with in a while, and I hope that next time I can thank her personally. From my friends and I, we thank you for sharing your home with us. If you think that the excellent reviews are too good to be true, don't. This IS the truth, and I can't wait to have another reason to come back to this wonderful treasure of a place.

Family-friendly home rentals with a pool

Guest favorite
Townhouse in Dover
4.96 out of 5 average rating, 148 reviews

Bear's Den - Mt Snow Townhome w/ Heated Pool!

NikkiRating, 5 stars2 months ago
Had a great time! Within 4 minutes of a stellar breakfast at Trail 87 and within 5 min of mount snow base.
Guest favorite
Condo in Dover
4.87 out of 5 average rating, 239 reviews

Mt Snow Ski In/Out at Seasons

MarkRating, 5 stars1 week ago
The unit is very comfortable for a family and very convenient to Mount Snow. Updated bathrooms and washer/dryer. Great clubhouse and pool facilities at Seasons condo. Andrew was a pleasure to work with.
Guest favorite
Bungalow in Easthampton
4.92 out of 5 average rating, 497 reviews

The Creation Station

AliyaRating, 5 stars2 weeks ago
John was incredible and so hospitable. His home was beautiful and well kept. Very responsive and one of the best weekends of the weekend ! 11/10 recommend :)
Top guest favorite
Home in Dover
5 out of 5 average rating, 58 reviews

The Villa - Industrial Farmhouse with Hot Tub

StephanieRating, 5 stars3 months ago
We absolutely loved staying here- beautiful and laid out perfectly for 2 families, each with 2 little kids. Super convenient location to Mt. Snow. We look forward to staying here again!
Superhost
Home in Surry
4.7 out of 5 average rating, 44 reviews

Bright, Large, Spacious Family Home

MaryRating, 5 stars5 months ago
We had a very relaxing stay. Plenty of space to stretch out. Located within 10-15 min. of Keene State activities, the purpose of our trip. Bryan was a wonderful host. Very responsive. Instructions were clear, directions very helpful. Everything we needed!!
Guest favorite
Home in Canaan
4.99 out of 5 average rating, 86 reviews

Berkshire Lake House, gunite pool, Chef's Kitchen

lisaRating, 5 stars2 months ago
Twelve members of our family stayed here for our annual ski weekend at Jiminy Peak. It was exactly what we needed as our home base -- plenty of room for all of us, good amenities, and the living room gave us a large gathering space where we could all sit after a day of skiing and swap stories, play games, and just enjoy being together. The house was very clean, well-stocked, and the owners were really responsive. We highly recommend it!
Guest favorite
Condo in Hancock
4.85 out of 5 average rating, 151 reviews

Cozy Condo @ Jiminy Peak

ElizabethRating, 5 stars2 months ago
We always book with Dawn! Her place is amazing. We feel right at home. She ensures the house has everything you could need in case you forget something. There are extra details to make your stay more comfortable. Her linens are softer than mine at home! There is plenty of space for my family of five to stay comfortably. I highly recommend booking here! We can’t wait until our next stay here.
Guest favorite
Apartment in Northampton
4.97 out of 5 average rating, 360 reviews

1880s sun-bathed beauty in best downtown location

MarissaRating, 5 stars2 weeks ago
The place was excellent. Around the corner from a great coffee shop, though it has a coffee machine and creamer provided for those that don't want to leave in the morning. Close to the main town but quiet. Sculptures that I want for my own house. Comfy beds. Well stocked kitchen. Easy to get in and out. Spacious. Good price. I will absolutely be looking to see if it is available next time I am in Northampton.

Quick stats about vacation rentals that are family-friendly in Charlemont

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ624 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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