Holiday houses in Chapel Falls

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Top-rated holiday rentals in Chapel Falls

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Wilmington

5 out of 5 average rating, 8 reviews

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

DevonRating, 5 stars3 months ago
Our family has been going to VT in the fall for 25+ years. The usual house we stay in was unavailable and lead us to find this home. Upon arrival we were stunned at the view, it is incredible in person! We had 5 adults and two children o this trip and this home offered us so much space and activities. My father even noted how everyone had their own space to dow whatever they wanted at any point in the day. We utilized the amenities every day and my kids were thrilled to have all the games to play inside as well as a beautiful lawn to run around and play on. Just a short drive down the driveway you reach the water which we also utilized mulitple times a day. Overall it was very peaceful and felt like a retreat and now my kids prefer this house over the old one! Definitely hoping to come back soon! Also, the hosts were very communicative and responsive before and during our stay, we very much enjoyed our time.
Guest favourite

Home in Hoosick Falls

4.91 out of 5 average rating, 11 reviews

Enjoy Fall & Experience Beautiful Changing Colors

AshleyRating, 5 stars4 months ago
Would highly recommend this beautiful spot!!! We loved the peaceful location and space for our entire family with the comforts of home in each room. Lots of extra pillows, towels, blankets, etc. fully stocked kitchen too. My kids wanted to stay longer, they had a great time. We will certainly come back!!
Guest favourite

Home in Pittsfield

4.97 out of 5 average rating, 111 reviews

Berkshire Lake- Modern and Updated-close to skiing

SameeraRating, 5 stars1 month ago
We had a wonderful stay at this lovely place! The owner was incredibly helpful and ensured we had a great experience. The location was truly magical, especially with the snow during Christmas, which added to the scenic beauty. There were plenty of nearby options for skiing and snow tubing, making it a perfect winter getaway. We highly recommend this spot for anyone looking for a cozy and picturesque retreat!
Superhost

Home in Great Barrington

4.88 out of 5 average rating, 102 reviews

Great Barrington, Cabin Sleeps 14, Walk To Town

HilaryRating, 5 stars1 week ago
Lucas’s home was perfect for a weekend getaway with a group of friends for a birthday celebration! Cozy and comfy sleeping spaces, great kitchen for cooking meals together, and perfect to stroll into town! Lucas was easily reached when a few minor questions came up and responded within minutes! Highly recommend!
Guest favourite

Home in Great Barrington

4.95 out of 5 average rating, 20 reviews

Luxury Redo: Hot Tub, Playroom, Sleeps 12

SarahRating, 5 stars7 months ago
The house is set back from the road in an inviting tree lined yard and felt “tucked in”. Loved the house book with detailed instructions. The hot tub was pretty easy to use - just a few missteps on our part. Every level had great amenities. All three beds we used were extraordinarily comfortable. Bathrooms extraordinarily clean!!
Guest favourite

Apartment in Wilmington

4.91 out of 5 average rating, 129 reviews

Globetrotter Retreat too - Minutes to the Mountain

RichardRating, 5 stars6 days ago
This is our second stay at this location (different apartment in same building) and it was very centrally located and close to Mount Snow. This is a great place to stay in Wilmington.
Superhost

Cottage in Great Barrington

4.83 out of 5 average rating, 36 reviews

THE GREAT ESCAPE BERKSHIRE SKI COTTAGE w/HOT TUB!

MaureenRating, 5 stars2 days ago
A large, lovely, comfortable home, (comfy beds, plush, plentiful linens) in a great location! Loads of room for six adults, two kids and our pup. We want to make it a yearly event!
Guest favourite

Villa in Pownal

4.94 out of 5 average rating, 66 reviews

Vermont Vacation Villa—Grapevine Getaway

DavidRating, 5 stars2 days ago
A GREAT stay! We had a family weekend away here, the place was big enough to fit all of us with plenty of space. There is a TON of space in this home with large rooms! The great room has a beautiful view of the scenery, kitchen is well stocked with the essentials, and garage was great to keep ski gear in while we were not at the mountain. Would highly recommend staying here and our family would love to return!
Superhost

Home in Readsboro

4.86 out of 5 average rating, 125 reviews

December in Peaceful Vermont (Pet Friendly)

JudahRating, 5 stars1 month ago
This stay was an absolute gem! The host’s charming old house radiates character and warmth, with every detail carefully curated to make you feel at home. Her hospitality was unmatched—gracious, attentive, and genuine. Clear directions were thoughtfully placed everywhere, making the stay seamless and stress-free.
Guest favourite

Home in Sheffield

4.9 out of 5 average rating, 115 reviews

Wow! Best BERKSHIRE SnowHome #1 Private SuperClean

JohannaRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay in Sally’s cozy apartment! It is well appointed and tastefully decorated. Sally was very responsive and caring. The beautiful views out of our bedrooms onto the garden and the wide open landscape behind it were major treats, especially on the morning after a heavy snowfall. We found everything we needed and more than expected - and hope to be back one day! Thank you very much, Sally!
Guest favourite

Home in Wilmington

5 out of 5 average rating, 25 reviews

Kiki's Mountain Chateau

AmyRating, 5 stars1 week ago
Had a weekend stay here and couldn’t have asked for a better place. Biggest thing is make sure you have AWD/4WD as the roads around are dirt roads and very snowy. My jeep however loved it. Very convenient commute to Mount Snow.
Guest favourite

Apartment in Williamstown

5 out of 5 average rating, 118 reviews

Downtown | Waterfront | Walk to Shops

JamelleRating, 5 stars3 weeks ago
I had an excellent time staying in Williams’ place. It was easy to find easy to get into and very convenient. Would highly recommend.

Popular amenities for Chapel Falls holiday rentals

Other great holiday rentals in Chapel Falls

Guest favourite

Home in Wilmington

5 out of 5 average rating, 10 reviews

Countryside SKI Retreat - Indr Pool&HotTubGameRoom

PhillipRating, 5 stars2 weeks ago
This was a great place for a family get away. Right in the middle of Southern VT ski country. Easy to get to both the Mount Snow area and downtown Wilmington. Club house at Chimney Hill was awesome. We utilized the fitness center each day and there were plenty of people enjoying the indoor pool. We also had a chance to do some ice skating. The house had plenty of room and we had a great time just gathering near the fireplace and watching the snow fall. Shannon and Erika were great hosts and let us know what to expect every step of the way. We look forward to returning to the area and making more memories with our family.
Guest favourite

Cottage in Woodford

4.95 out of 5 average rating, 42 reviews

HoneyBear Lake Cottage

CarinaRating, 5 stars5 months ago
We had a wonderful peaceful stay at Honey Bear, Linda Jane is a fantastic host and her home is beautiful and relaxing. It rained a lot of our stay, but we did get to make the most of our stay when it was nice out with all the wonderful inclusions. The boats and games were a fanatic added bonus. Thank you so much
Guest favourite

Home in Granby

5 out of 5 average rating, 6 reviews

Lake house retreat Granby CT

ChristeRating, 5 stars2 months ago
WENT FOR A FAMILY CELEBRATION FOR THANKSGIVING WEEKEND. THE HOUSE WAS INCREDIBLY STUNNING, GREAT ENTERTAINMENT AREAS, PLENTY OF SEATING, BEAUTIFUL KITCHEN. EVEN THOUGH IT WAS THE END OF NOVEMBER, WE STILL WERE ABLE TO USE ALL THE OUTSIDE AMENITIES, THE OUTDOOR BAR, SEATING AREA, FIRE PIT, THE HEAT LAMPS WERE PERFECT & UNEXPECTED. THE OUTDOOR AREA WAS AS AMAZING AS INSIDE. THE HOUSE WAS BETTER THAN WE EXPECTED, WOULD HAVE TO SAY PERFECTION! CANNOT WAIT TO GO STAY AGAIN. THANK YOU TO NATHANIA, YOU'RE COMMUNICATION WITH US WAS QUICK & GREATLY APPRECIATED! LOVED EVERY MINUTE!
Guest favourite

Home in Charlemont

4.94 out of 5 average rating, 53 reviews

Tall Pines Rental

RamonaRating, 5 stars2 weeks ago
The house was spectacular. Beautiful, large open space in a private setting, but close to town. Large kitchen with lots of counter space. The entire first floor is an open area. It was perfect for my husband and myself and our daughter and her friends. There’s a beautiful dining table. Nice TV set up with comfy seating. And pool table that kept us all entertained for hours. The master bedroom is on the first floor, and two bedrooms with single beds are on a second floor with a balcony overlooking the large living area. An unexpected snow storm came in while we were there and after reaching out to the owner he got back to me right away regarding having the driveway plowed out the following morning. The house was well equipped and the check out process was very easy. I loved it and would definitely stay there again.
Guest favourite

Home in Monroe

4.92 out of 5 average rating, 13 reviews

The Camp

BrendaRating, 5 stars1 day ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Superhost

Home in Wilmington

5 out of 5 average rating, 11 reviews

Outdoor Enthusiasts Paradise!

EmilyRating, 5 stars2 weeks ago
Our family had a beautiful, peaceful ski/snowboard vacation at Samantha’s home. The house was exceptionally clean and Samantha was an attentive host. We’ll hopefully visit again!
Superhost

Home in Halifax

4.88 out of 5 average rating, 48 reviews

Rural VT Retreat—Complete Privacy on 140 Acres!

MarisaRating, 5 stars1 month ago
We had a wonderful weekend at the house. The hot tub was fantastic and the huge living room was perfect for my group to just hang out and enjoy each other’s company. Would absolutely stay here again!
Guest favourite

Cabin in Wilmington

5 out of 5 average rating, 72 reviews

Stoni Woods: Log Home in Southern VT

CharlesRating, 5 stars3 weeks ago
We had a wonderful time at Beth's Stoni Woods house. The house itself is lovely and we also liked the large garage/basement for loading/unloading things in the snow. Beth was very responsive and had answers to any questions we had. Overall a great stay and we would stay again.

Destinations to explore

  1. Airbnb
  2. United States
  3. Massachusetts
  4. Franklin County
  5. Ashfield
  6. Chapel Falls