A small town with a church, houses, and a lake surrounded by autumn-colored trees.

Holiday Homes in Chelsea

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chelsea holiday homes

A cozy living room with a sofa, armchair, and a bookshelf. There is a fireplace and a window providing natural light.

1. Authentic farmhouse for those who love cozy, quirky, historical imperfection

Authentic farmhouse for those who love cozy, quirky, historical imperfection
Randolph Center
10.0 out of 10, Exceptional, (6 reviews)
"The rental experience was seemless....communication was great, the property fit our family so easily and the location was easily accessible to many beautiful spots. The home is well equipped and it was a delightful stay!"
United States
Kathy K.
The price is AU$953
includes taxes & fees
28 Oct - 29 Oct
Authentic farmhouse for those who love cozy, quirky, historical imperfection
A room with a large window overlooking a forest in autumn.

2. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.4 out of 10, Exceptional, (50 reviews)
"Nice location off of Route 100 there was a little road noise but the house is situated a bit back. The seating was super comfy and the kitchen was nicely stocked for cooking. It was awesome to be able to bring our pup! "
United States
Melissa P.
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

3. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (27 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
A rustic cabin surrounded by autumn foliage.

4. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.0 out of 10, Wonderful, (12 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
Beautiful home located in the Mad River Valley
A room with a wooden wall, a blue sofa, a dartboard, and a poster.

5. The Willard House | Large Vermont Retreat | Hot Tub + Game Room

The Willard House | Large Vermont Retreat | Hot Tub + Game Room
Bradford
The price is AU$1,068
includes taxes & fees
13 Oct - 14 Oct
The Willard House | Large Vermont Retreat | Hot Tub + Game Room
A house with a stone staircase leading to a wooden deck, surrounded by lush greenery.

6. Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush

Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
East Warren
9.6 out of 10, Exceptional, (18 reviews)
"Great location, plenty of space, everything in house worked as described. Thank you!!"
United States
Daniel B.
Hand Crafted Post and Beam Home with Mountain Views Minutes from Sugarbush
A two-story house with a covered porch, outdoor seating, and a lawn.

7. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.4 out of 10, Exceptional, (59 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
Classic Vermont Farmhouse near Sugarbush Resort
A room with a large window overlooking a deck with two chairs and a table.

8. Luxurious Vermont home minutes from Sugarbush Resort

Luxurious Vermont home minutes from Sugarbush Resort
Warren
10.0 out of 10, Exceptional, (44 reviews)
"Perfect location for ski vacation. House was clean, close to resort. Quick drive to restaurants, looking forward to staying again! "
United States
Noah S.
Luxurious Vermont home minutes from Sugarbush Resort
A spacious living area with a fireplace, a curved staircase, and large windows offering views of the outdoors.

9. The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views

The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views
East Warren
10.0 out of 10, Exceptional, (7 reviews)
"Gorgeous house in amazing location!"
United States
Brian S.
The price is AU$1,971
includes taxes & fees
22 Oct - 23 Oct
The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views
A covered porch with a view of a white house and a green lawn.

10. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
9.6 out of 10, Exceptional, (4 reviews)
"5 bedrooms with only 2.5 baths but beautiful!"
United States
Jamie R.
The price is AU$1,969
includes taxes & fees
13 Oct - 14 Oct
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
An outdoor seating area with wicker chairs and a small table, surrounded by lush greenery and trees.

11. Entire Enchanting, Light-Filled 1830 Farmhouse

Entire Enchanting, Light-Filled 1830 Farmhouse
Waitsfield
9.8 out of 10, Exceptional, (10 reviews)
"We came up to Vermont for a wedding and the "farm house" was just what we needed. Thank you! Much appreciated the easy check in and allowing us to arrive a bit earlier to get ready for the wedding bash. P. Murray"
United States
Patti M.
The price is AU$1,048
includes taxes & fees
19 Oct - 20 Oct
Entire Enchanting, Light-Filled 1830 Farmhouse
A wooden deck with a hot tub and seating, overlooking a scenic landscape.

12. Sky Zen - Ridge Line Retreat

Sky Zen - Ridge Line Retreat
East Warren
10.0 out of 10, Exceptional, (1 review)
"We've stayed multiple times in this property and it's always been great. Beautiful house, landscape, and of course the views. The house is always very clean and well maintained. We look forward to our next stay here."
United States
Spyridon M.
The price is AU$1,421
includes taxes & fees
8 Nov - 9 Nov
Sky Zen - Ridge Line Retreat
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

13. Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace

Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
Hancock
10.0 out of 10, Exceptional, (1 review)
"The maple castle was awesome! Definitely the most unique house I have ever stayed in. You can sit in the hot tub and watch the river or you can walk down a tiny hill to tie up a tube and float in it. The owners were extremely helpful and responsive. Would definitely recommend. "
United States
Katie H.
The price is AU$1,965
includes taxes & fees
25 Oct - 26 Oct
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
A living room with a brown leather sofa, a round coffee table, and a vase of flowers.

14. Renovated Modern Chalet in Mad River Valley

Renovated Modern Chalet in Mad River Valley
Warren
The price is AU$992
includes taxes & fees
18 Oct - 19 Oct
Renovated Modern Chalet in Mad River Valley
A two-story house with a fenced backyard, outdoor seating, and a fire pit.

15. Wilder Farm--Charming Vermont Farmhouse in Mad River Valley

Wilder Farm--Charming Vermont Farmhouse in Mad River Valley
Waitsfield
The price is AU$2,212
includes taxes & fees
18 Oct - 19 Oct
Wilder Farm--Charming Vermont Farmhouse in Mad River Valley
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Great place,"
Ivan 1-night trip
Posted 1 hour ago
My Place Hotel-Randolph VT

Find out more about Chelsea

Chelsea Holiday Homes information

Number of reviews
180
Accommodation
210 Holiday Homes
Lowest Price
AU$953
Highest Price
AU$2,212