Chelsea Holiday Rentals

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Our top choices for Chelsea holiday rentals

10.0 out of 10, Exceptional, (38)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is HK$1,168
HK$1,500 total
includes taxes & fees
2 Jan - 3 Jan 2026
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
10.0 out of 10, Exceptional, (272)
"Very beautiful little cabin and very private we are definitely keeping this on are favorites list so we can stay again "
United States
Kevin B.
Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (530)
"We had such an amazing trip! We were able to ski Killington, Okemo and Stowe while staying there. The cabin was so cozy and the beds were very comfortable. The host was excellent and checked in to ensure everything was just perfect. The cabin is very charming and it was beautiful to watch the snow fall while sitting in front of the toasty fireplace. 1000 percent would stay again!!! Lots of love went in to making this cabin for sure. It truly felt magical for the week we were there."
United States
Brooke
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Condo resort in Warren

Bridges Resort
3.5 star property
8.2 out of 10, Very good, (16)
"Great condo and excellent proximity to sugarbush. 10/10 would rent again"
United States
Jesse
The price is HK$1,442
HK$1,917 total
includes taxes & fees
7 Jan - 8 Jan 2026
Bridges Resort
9.8 out of 10, Exceptional, (159)
"Great location and a great price. Perfect for 2-4 people who just want to get away to the peace of Vermont."
United States
James N.
The price is HK$1,681
HK$3,400 total
includes taxes & fees
16 Dec - 17 Dec
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (20)
"Very clean and perfect for our group. "
United States
Kimberly P.
4BR Retreat w/ Hot Tub, Fire Pit, Basketball Court, Hammock, Patio, Near lake
8.4 out of 10, Very good, (74)
"Perfect summer getaways! The condo was comfortable and in a great location. The pools and rec center were also so much fun. Looking forward to coming back next year."
United States
Christine P.
The price is HK$638
HK$1,844 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lovely condo near skiing with 3 pools, hot tub, sauna, fitness room & balcony
8.8 out of 10, Excellent, (22)
"Ideally located for any season "
United States
Alison M.
The price is HK$592
HK$2,726 total
includes taxes & fees
18 Dec - 19 Dec
Ski getaway near the slopes with private balcony & mountain views
9.8 out of 10, Exceptional, (39)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
United States
Dmitriy K.
Beautiful home located in the Mad River Valley
10.0 out of 10, Exceptional, (37)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is HK$981
HK$1,831 total
includes taxes & fees
16 Dec - 17 Dec
Secluded retreat in the trees
9.0 out of 10, Wonderful, (43)
"Has everything you need for a great Summer stay!"
United States
Ashley G.
Relaxing Ski Condo with Pools, Hot Tub, and Entertainment - Near Ski Access
9.0 out of 10, Wonderful, (19)
"We really enjoyed our stay. The view of the mountains from the deck is fantastic and the place is large and comfortable. We enjoyed the pool table and the comfortable beds. It feels remote but it’s a short drive to Montpelier. We would stay again!"
Canada
Laurel A.
Dog-friendly home with panoramic mountain views, grill, deck, & pool table
9.6 out of 10, Exceptional, (16)
"Just as described, perfect for a family vacation."
United States
Jennifer K.
Ski-in/out condo steps from the lifts/village with fireplace & mountain views
10.0 out of 10, Exceptional, (82)
"The condo was close to everything, spacious, clean, and comfortable! Would definitely stay there again. "
United States
Lori C.
Ski-on/Off, Slope Views, Mountainside Top Floor, Vaulted Ceilings, Gas Fireplace
10.0 out of 10, Exceptional, (15)
"We had a great time - pool and hot tub were a blast for the kids! "
United States
Sheila Dillon W.
Beautiful brand new cabin one minute from Sugarbush Resort
9.4 out of 10, Exceptional, (30)
"Beautiful home and great for a group ski trip. Owner was attentive and helpful. "
United States
David K.
SugarBush Valley, Mad River Valley, Warren VT; Weekly, Monthly Discounted rates
9.8 out of 10, Exceptional, (52)
"We stayed here with friends in the summer! Plenty of space for kids, and they loved the loft space! Would be a great ski location with lots of beds!"
United States
Kate C.
SPACIOUS CHALET!! Ski, Golf, Tennis, Hiking, Mountain Biking!! Early discounts!
The price is HK$778
HK$2,295 total
includes taxes & fees
17 Dec - 18 Dec
Ski-in/ski-out ground floor condo near slopes, balcony, fireplace, pool, wifi
9.2 out of 10, Wonderful, (26)
"Great little cabin perfect for everything I needed. definitely will stay again.. very peaceful, great place unwind. "
United States
Michael R.
Charming cabin located one minute from the base of Sugarbush Resort
9.8 out of 10, Exceptional, (21)
"Great dog freindly cabin. Love the hot tub! Just as good as the first time,"
United States
Jack G.
Lovely cabin nestled in the woods one minute from Sugarbush Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chelsea Hotel Reviews

Find out more about Chelsea

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Frequently asked questions

Can I find a holiday rental in Chelsea?

Yes, there are holiday rentals close to the most popular sights in Chelsea, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chelsea has to offer?

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you: This highly rated holiday home rental in Chelsea offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Chelsea?

While exploring the area, visit family-friendly sights like Rock of Ages, or get outside and enjoy nature at Lake Fairlee. Other places in town to visit include Chelsea Public Library and Alden Speare Memorial Library.

What’s a holiday rental in Chelsea like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chelsea. Holiday rentals provide amenities like WiFi and washers and dryers so your stay will be comfortable. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.