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Chelsea Holiday Rentals

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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 rentals

A living room with a fireplace, a painting, shelves with decorative items, and a television.

1. Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (50 reviews)
"We enjoyed our stay, property was as described. It's convenient to many of the Hudson Valley small towns, including West Point."
United States
Mike W.
The price is HK$1,059
HK$2,326 total
includes taxes & fees
19 Oct - 20 Oct
Grant - A Tranquil One Bedroom Steps from River
A cozy living room with a sofa, a dining table, and a bed.

2. Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
10.0 out of 10, Exceptional, (75 reviews)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is HK$1,452
HK$2,772 total
includes taxes & fees
18 Oct - 19 Oct
Cozy country efficiency in the Hudson Valley
A brick building with a sign reading 'Lobby' in front.

3. Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill

Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
Fishkill
9.2 out of 10, Wonderful, (20 reviews)
"Great place to stay,"
United States
Anonymous traveller
The price is HK$621
HK$717 total
includes taxes & fees
12 Nov - 13 Nov
Cozy Queen Suite, Nsmk Kitchen|Studio 6 Fishkill
A compact living space with a kitchenette, a sofa, a bed, and a colorful rug.

4. Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (36 reviews)
"Great place! Nicely decorated with attention to detail. My wife and I would stay again if we are back in the area."
United States
Tim G.
The price is HK$981
HK$1,789 total
includes taxes & fees
18 Oct - 19 Oct
Cabin in the Heart of the Hudson Valley, Cabin 1
An outdoor patio area with a covered seating area, a pool, and potted plants.

5. Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.2 out of 10, Wonderful, (80 reviews)
"It’s was nice, clean and the outdoor out area was really nice."
United States
Roger S.
The price is HK$2,158
HK$2,840 total
includes taxes & fees
28 Oct - 29 Oct
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
A hotel lobby with a reception desk, seating area, and a fire extinguisher on the wall.

6. 1 King Bed | Non-Smoking, Kitchen, Shower

1 King Bed | Non-Smoking, Kitchen, Shower
Fishkill
9.6 out of 10, Exceptional, (19 reviews)
"Great rooms and service,"
United States
Anonymous traveller
The price is HK$621
HK$702 total
includes taxes & fees
26 Oct - 27 Oct
1 King Bed | Non-Smoking, Kitchen, Shower
A small, two-story house with a red and gray exterior, a front porch with blue chairs, and a table.

7. Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (31 reviews)
"Everything was just as it was in our past stays. The place was clean, neat and organized very well. Communication with the host was very easy and almost immediate reply."
United States
Albert
The price is HK$903
HK$1,493 total
includes taxes & fees
20 Oct - 21 Oct
Cabin in the heart of the Hudson Valley, Cabin 4
A modern kitchen with grey cabinets, stainless steel appliances, a granite countertop, and a wooden floor.

8. 2-bedroom apartment in excellent Newburgh with AC and charm

2-bedroom apartment in excellent Newburgh with AC and charm
Newburgh
10.0 out of 10, Exceptional, (3 reviews)
"We have stayed here once before overnight while in the area for an event. It is close to where we needed to be and a great value for the price"
United States
Nick L.
The price is HK$1,483
HK$1,909 total
includes taxes & fees
25 Oct - 26 Oct
2-bedroom apartment in excellent Newburgh with AC and charm
An aerial view of a lakeside property with a dock, a small building, and several outdoor seating areas.

9. Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Clean rooms, Diner down the block, family friendly, communication was prompt and clear"
United States
Joseph
The price is HK$1,968
HK$3,065 total
includes taxes & fees
6 Nov - 7 Nov
Rustic Cabin in Fishkill!
A stone house with a steeply pitched roof, surrounded by a well-maintained lawn and trees.

10. Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed a relaxing weekend before R-day at West Point and it was perfect! A beautiful property and we hope to be back another time!"
United States
Quintina R.
The price is HK$3,021
HK$4,415 total
includes taxes & fees
11 Nov - 12 Nov
Chestnut on Willow Lake
A brown backpack leaning against a wall, a pair of brown shoes on a black mat, and a view of a porch with a wicker chair and a white cushion.

11. Private River View Deck · Walk Downtown

Private River View Deck · Walk Downtown
Newburgh
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,399
HK$3,773 total
includes taxes & fees
3 Nov - 4 Nov
Private River View Deck · Walk Downtown
A brick building with a sign reading 'Lobby' in front.

12. 2 Full Beds | Non-Smoking, Kitchen

2 Full Beds | Non-Smoking, Kitchen
Fishkill
9.2 out of 10, Wonderful, (21 reviews)
"great place tostay"
United States
Anonymous traveller
The price is HK$683
HK$789 total
includes taxes & fees
1 Nov - 2 Nov
2 Full Beds | Non-Smoking, Kitchen
A lakeside seating area with Adirondack chairs arranged around a central fire pit.

13. Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is HK$2,158
HK$3,245 total
includes taxes & fees
15 Nov - 16 Nov
Red Cottage - Lakeside Property!
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

14. Bright Cornwall-on-hudson Vacation Rental!

Bright Cornwall-on-hudson Vacation Rental!
3.0 star property
Cornwall
10.0 out of 10, Exceptional, (1 review)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
United States
Poyuk
Bright Cornwall-on-hudson Vacation Rental!
A staircase with red carpeted steps, wooden handrails, and string lights.

15. Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (17 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is HK$3,610
HK$4,848 total
includes taxes & fees
1 Nov - 2 Nov
Large,Cozy,Bright Apartment, Business Themed.
A small blue house with two blue Adirondack chairs, a small table, and a potted plant.

16. Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (41 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is HK$903
HK$1,493 total
includes taxes & fees
18 Oct - 19 Oct
Cabin in the heart of the Hudson Valley, Cabin 2
A single-story house with a front porch, two blue chairs, a white chair, and a potted plant with pink flowers.

17. Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (20 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$981
HK$1,808 total
includes taxes & fees
20 Oct - 21 Oct
Cabin in the heart of the Hudson Valley, Cabin 3
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

18. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.2 out of 10, Wonderful, (25 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is HK$902
HK$2,437 total
includes taxes & fees
18 Oct - 19 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern kitchen with white cabinets, a central island with stools, a stainless steel refrigerator, and a staircase leading to another level.

19. Bright Cornwall-On-Hudson Vacation Rental!

Bright Cornwall-On-Hudson Vacation Rental!
Cornwall-On-Hudson
10.0 out of 10, Exceptional, (35 reviews)
"We had a girlfriend get away long weekend. This was a great house and really convenient location. Two really good restaurants were within walking distance just around the corner. I would highly recommend staying here!"
United States
Dawn H.
The price is HK$2,409
HK$5,608 total
includes taxes & fees
22 Oct - 23 Oct
Bright Cornwall-On-Hudson Vacation Rental!
A rustic cabin with a chimney, surrounded by dense autumn foliage and a narrow road.

20. Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
Hopewell Junction
9.4 out of 10, Exceptional, (13 reviews)
"Lovely space and situation, unique. Close to the AT, as well."
United States
Peter W.
The price is HK$1,326
HK$2,193 total
includes taxes & fees
18 Oct - 19 Oct
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Parking was great, very clean, friendly and helpful staff, and some good breakfast. Thank you for making my stay enjoyable!"
Natasha 1-night trip
Posted 1 hour ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Chelsea

Search for holiday rentals in Chelsea on Expedia! You can easily find your home rentals, villas, holiday apartments in Chelsea using one of the methods below:

  • View our selection of featured holiday rentals in Chelsea
  • Use the map to find apartments and other holiday homes in the Chelsea neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chelsea while they last

Look no further and take a look at our great range of rental properties in Chelsea!

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?

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views: This holiday home rental outside of Chelsea is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

What can I see and do in Chelsea?

While exploring the area, visit family-friendly sights like SplashDown Beach, or get outside and enjoy nature at Bowdoin Park. In the wider area, you’ll find Benmarl Vineyards and Winery and Dia Beacon.

What are holiday rentals like in Chelsea?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chelsea. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip.