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

Chelsea Holiday Rentals

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Our top choices for Chelsea holiday rentals

1. Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich

Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich
Williamstown
10.0 out of 10, Exceptional, (61 reviews)
"Very peaceful setting! Love the chairs on the back deck, looking out onto the yard. Everything was clean and well kept. Check-in was effortless. I would definitely stay here again."
United States
Heather
The price is NZ$334
includes taxes & fees
31 Aug - 1 Sept
Central to VT skiing areas 5 minutes to I-89 , near VAST trails, near Norwich

2. Brand New Cabin On Working Farm

Brand New Cabin On Working Farm
Northfield
9.8 out of 10, Exceptional, (29 reviews)
"No one ever greeted us except the dogs but everything else was very good including useful kitchen goods. Bathroom door needs to be lubricanted."
United States
Michael
The price is NZ$304
includes taxes & fees
25 Aug - 26 Aug
Brand New Cabin On Working Farm

3. 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 NZ$1,184
includes taxes & fees
30 Aug - 31 Aug
Authentic farmhouse for those who love cozy, quirky, historical imperfection

4. Brookside Cabin - Your Peaceful VT Off-Grid Escape

Brookside Cabin - Your Peaceful VT Off-Grid Escape
Brookfield
The price is NZ$736
includes taxes & fees
31 Aug - 1 Sept
Brookside Cabin - Your Peaceful VT Off-Grid Escape

5. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (13 reviews)
"Such a beautiful home and property! Our host was amazing! I would recommend this property to anyone! Thank you! We loved our stay!"
United States
Meg K.
The price is NZ$516
includes taxes & fees
25 Aug - 26 Aug
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

6. Luxurious Renovated Farmhouse Post & Beam Barn and Charm

Luxurious Renovated Farmhouse Post & Beam Barn and Charm
Williamstown
9.4 out of 10, Exceptional, (49 reviews)
"We had such a great time during our stay! The house was beautiful, warm and welcoming and we would gladly come back again! We had everything we needed for a relaxing weekend in. Host Ali was very friendly and communicative."
United States
Alison G.
The price is NZ$1,089
includes taxes & fees
25 Aug - 26 Aug
Luxurious Renovated Farmhouse Post & Beam Barn and Charm

7. One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!

One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!
Barre
8.8 out of 10, Excellent, (9 reviews)
"Place is great quiet comfy clean and so well equipped if available would definitely stay again"
United States
Brian
The price is NZ$423
includes taxes & fees
25 Aug - 26 Aug
One bedroom Apt- Part of a triplex in Barre Vermont! Great Price!

8. Charming TREEHOUSE in remote location

Charming TREEHOUSE in remote location
Braintree
10.0 out of 10, Exceptional, (1 review)
The price is NZ$738
includes taxes & fees
21 Sept - 22 Sept
Charming TREEHOUSE in remote location

9. Go Skiing or Hiking from an Enchanting, Light-Filled Home

Go Skiing or Hiking from an Enchanting, Light-Filled Home
Waitsfield
9.8 out of 10, Exceptional, (50 reviews)
"Excellent Location ! "
United States
Luke A.
The price is NZ$574
includes taxes & fees
25 Aug - 26 Aug
Go Skiing or Hiking from an Enchanting, Light-Filled Home

10. One Zero Five Stay 303

One Zero Five Stay 303
Barre
10.0 out of 10, Exceptional, (1 review)
"Spacious and clean. Multiple codes (to building and to apartment) were a little confusing, but worked."
United States
STEF Z.
The price is NZ$660
includes taxes & fees
21 Sept - 22 Sept
One Zero Five Stay 303

11. Addie's Place: A Quiet and Quirky Guesthouse

Addie's Place: A Quiet and Quirky Guesthouse
Hartford
9.4 out of 10, Exceptional, (16 reviews)
"Nice cottage setting in a quiet neighborhood, my dogs loved it!"
United States
Victor R.
The price is NZ$377
includes taxes & fees
25 Aug - 26 Aug
Addie's Place: A Quiet and Quirky Guesthouse

12. Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC

Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC
East Warren
The price is NZ$667
includes taxes & fees
25 Aug - 26 Aug
Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC

13. Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (20 reviews)
"Loved the property. Clean, modern, great location."
United States
Richard
The price is NZ$684
includes taxes & fees
25 Aug - 26 Aug
Dreamy Artist Chalet in Secluded Historic Village

14. Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (172 reviews)
"Jill was very attentive to make sure we had everything we needed very nice stay!"
United States
Kathy B.
The price is NZ$753
includes taxes & fees
25 Aug - 26 Aug
Stetson Hollow Cabin by Stetson Brook

15. Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit

Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit
East Warren
10.0 out of 10, Exceptional, (1 review)
"This was a beautiful VRBO clean, cozy and so well equipped. "
United States
Laura H.
The price is NZ$510
includes taxes & fees
25 Aug - 26 Aug
Sunny Alpine Suite • Walk to Lake • Private Deck • Yard and Gardens w/Fire Pit

16. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is NZ$871
includes taxes & fees
31 Aug - 1 Sept
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

17. Disco Den on Toad Road

Disco Den on Toad Road
Plainfield
10.0 out of 10, Exceptional, (2 reviews)
"All was good "
United States
Brian
The price is NZ$266
includes taxes & fees
9 Sept - 10 Sept
Disco Den on Toad Road

18. 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

19. Four Season Condo: ski, hike, mountain bike & seasonal pool

Four Season Condo: ski, hike, mountain bike & seasonal pool
Warren
The price is NZ$366
includes taxes & fees
25 Aug - 26 Aug
Four Season Condo: ski, hike, mountain bike & seasonal pool

20. Ski-in/ski-out condo with mountain view, seasonal pool

Ski-in/ski-out condo with mountain view, seasonal pool
Warren
The price is NZ$503
includes taxes & fees
25 Aug - 26 Aug
Ski-in/ski-out condo with mountain view, seasonal pool
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chelsea holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chelsea. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chelsea. Seeing all the best attractions is bound to make you fall in love with Chelsea. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chelsea short-term rentals, that won’t be hard to do.

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.

How many holiday rentals will I find in Chelsea?

Choose from 3 Expedia holiday rentals in Chelsea for a memorable holiday.

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.