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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 €523
includes taxes & fees
10 Nov - 11 Nov
Authentic farmhouse for those who love cozy, quirky, historical imperfection
A rustic cabin with a dirt path leading to it, surrounded by autumn foliage.

2. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.8 out of 10, Exceptional, (28 reviews)
"We had a great time! "
United States
Allie T.
The price is €236
includes taxes & fees
3 Nov - 4 Nov
Beautiful home located in the Mad River Valley
A rustic cabin with a dirt path leading to it, surrounded by autumn foliage.

3. 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.
The price is €236
includes taxes & fees
3 Nov - 4 Nov
Beautiful home located in the Mad River Valley
A two-story house with a covered porch, outdoor seating, and a lawn.

4. Classic Vermont Farmhouse near Sugarbush Resort

Classic Vermont Farmhouse near Sugarbush Resort
Warren
9.4 out of 10, Exceptional, (61 reviews)
"Great location for skiing at Sugarbush. Nice big living room for the whole group to gather. "
United States
Peggy V.
The price is €428
includes taxes & fees
3 Nov - 4 Nov
Classic Vermont Farmhouse near Sugarbush Resort
A cozy room with a table, a cup, a basket, and a heater.

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 €673
includes taxes & fees
1 Nov - 2 Nov
The Willard House | Large Vermont Retreat | Hot Tub + Game Room
A spacious living area with a fireplace, a curved staircase, and large windows offering views of the outdoors.

6. 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 €1,176
includes taxes & fees
8 Nov - 9 Nov
The Vines - 6000 sq. ft. Luxury Estate with Hot Tub & Mountain Views
A wooden deck with a table and chairs, surrounded by a railing with string lights.

7. Tiny House Woodland Retreat • Private Hot Tub • Sugarbush

Tiny House Woodland Retreat • Private Hot Tub • Sugarbush
East Warren
The price is €386
includes taxes & fees
2 Nov - 3 Nov
Tiny House Woodland Retreat • Private Hot Tub • Sugarbush
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a bar area with stools.

8. Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub

Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
Duxbury
9.8 out of 10, Exceptional, (12 reviews)
"This home was just what we needed to rest our heads while on a long road trip with the family."
United States
Martin H.
Brand new family home nestled in the woods close to Waterbury, Stowe, and Sugarbush with a hot tub
A log cabin interior with a stone fireplace, a sofa set, a round table, and a large window offering a view of the outdoors.

9. Ridge House - Modern Log Home Nestled on top of a Private Mountain

Ridge House - Modern Log Home Nestled on top of a Private Mountain
Waitsfield
10.0 out of 10, Exceptional, (18 reviews)
"Great property, would rent again in the future! "
United States
Stephen K.
The price is €856
includes taxes & fees
12 Nov - 13 Nov
Ridge House - Modern Log Home Nestled on top of a Private Mountain
A wooden deck with a hot tub and seating, overlooking a scenic landscape.

10. 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.
Sky Zen - Ridge Line Retreat
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 €642
includes taxes & fees
30 Oct - 31 Oct
Entire Enchanting, Light-Filled 1830 Farmhouse
A covered porch with a view of a white house and a green lawn.

12. 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 €1,260
includes taxes & fees
28 Nov - 29 Nov
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
A two-story yellow house with a porch, a front door, and a small front yard.

13. Charming Vermont Farmhouse in Mad River Valley

Charming Vermont Farmhouse in Mad River Valley
Waitsfield
The price is €1,248
includes taxes & fees
3 Nov - 4 Nov
Charming Vermont Farmhouse in Mad River Valley
A cozy living room with a stone fireplace, wooden walls, a leather sofa, and a dining area.

14. 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.
Maple Castle – Cozy Riverside Retreat with Hot Tub, Trails & Fireplace
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

Dowds Country Inn

Dowds Country Inn

10/10 Excellent
"Hallmark move over, quaint town, amazing breakfast, and a staff that is so kind. Loved my stay, especially love my apple/cinnamon pancakes. I literally saw them check in someone into a flight. Bend over backwards kind of staff."
amy 4-night trip
Posted less than an hour ago
Dowds Country Inn

Find out more about Chelsea

Chelsea Holiday Homes information

Number of reviews
160
Accommodation
210 Holiday Homes
Lowest Price
€236
Highest Price
€1,260