Chelsea Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Chelsea holiday rentals

Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (5 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$1,281
HK$2,405 total
includes taxes & fees
13 Apr - 14 Apr
Fabulous 3bdrm Home w/parking!
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (24 reviews)
"Serg’s place was comfortable and clean! It was a perfect location for me and my friends to stay while rock climbing in the Gunks. We did not feel cramped or unsafe and the complementary tea was a hit! One thing to note is that both of the beds were low to the ground (below knee level) so if someone has knee or back problems, it might be difficult to stand up out of bed. "
United States
Mary S.
The price is HK$426
HK$1,189 total
includes taxes & fees
2 Apr - 3 Apr
Dream getaway apartment in the foot of Gunks Ridge
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (1 review)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
Cozy 1-bedroom retreat minutes from West Point!
Property grounds

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.

Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Carmel Hamlet
10.0 out of 10, Exceptional, (2 reviews)
"Great place, responsive host. Would return!"
United States
Brian S.
Enchanting Lake front chalet with backyard and fire pit. Dog friendly.
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (134 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,473
HK$2,384 total
includes taxes & fees
2 Apr - 3 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Terrace/patio

House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!
Highland Falls
10.0 out of 10, Exceptional, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is HK$980
HK$3,049 total
includes taxes & fees
2 Apr - 3 Apr
House on the Babbling Brook- Quiet 2BR + King Bed!
Exterior detail

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work

Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Putnam Valley
9.8 out of 10, Exceptional, (23 reviews)
"Great, clean house, nice accommodating host. Would stay here again. "
United States
Heather T.
The price is HK$1,306
HK$3,818 total
includes taxes & fees
8 Apr - 9 Apr
Walk-to-Lake Cottage With Office for Quiet Days and Easy Work
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is HK$795
HK$1,609 total
includes taxes & fees
14 Apr - 15 Apr
Historic Cabin with Pool & Fire Pit
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.0 out of 10, Wonderful, (26 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is HK$1,011
HK$1,564 total
includes taxes & fees
6 Apr - 7 Apr
Cabin in the heart of the Hudson Valley, Cabin 4
Private kitchen

Charming 1-bedroom apartment in Carmel with WiFi, AC

Charming 1-bedroom apartment in Carmel with WiFi, AC
Carmel Hamlet
9.0 out of 10, Wonderful, (2 reviews)
"Didn’t expect the layout separate entrance. Very clean and great amenities. Highly recommended and very nice family. "
United States
Emmett
The price is HK$1,058
HK$2,174 total
includes taxes & fees
6 Apr - 7 Apr
Charming 1-bedroom apartment in Carmel with WiFi, AC
Fridge, oven, stovetop, coffee/tea maker

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

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (18 reviews)
"Great Unit."
United States
Rudy R.
The price is HK$901
HK$2,387 total
includes taxes & fees
6 Apr - 7 Apr
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Property grounds

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!

Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Wallkill
10.0 out of 10, Exceptional, (79 reviews)
"great location and nice host"
United States
christopher s.
The price is HK$1,094
HK$2,086 total
includes taxes & fees
2 Apr - 3 Apr
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
1 bedroom, iron/ironing board, free WiFi, bed sheets

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, (32 reviews)
"Great overnight spot, especially with a dog."
United States
Ed C.
The price is HK$1,324
HK$2,212 total
includes taxes & fees
6 Apr - 7 Apr
Cabin in the Heart of the Hudson Valley, Cabin 1
TV, fireplace

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Carmel Hamlet
9.8 out of 10, Exceptional, (13 reviews)
"We loved the cleanliness, the location near the lake and the neighborhood restaurant, The Great Blue Heron."
United States
Hannah P.
The price is HK$1,587
HK$3,121 total
includes taxes & fees
2 Apr - 3 Apr
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Exterior detail

Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.
New Paltz
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is HK$960
HK$1,909 total
includes taxes & fees
13 Apr - 14 Apr
Cozy private suite in the heart of beautiful Gardiner.
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Clean, simple, and comfortable with clear host directions on arrival, checkin & checkout."
United States
Lou F.
The price is HK$1,293
HK$2,453 total
includes taxes & fees
3 Apr - 4 Apr
Cozy country efficiency in the Hudson Valley
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (49 reviews)
"Great place!"
United States
Sara B.
The price is HK$902
HK$1,958 total
includes taxes & fees
7 Apr - 8 Apr
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Outdoor dining

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
9.4 out of 10, Exceptional, (62 reviews)
"For us it was in a great location, had a reasonable price and room for everyone."
United States
Gertrude (Gert) P.
The price is HK$1,939
HK$2,532 total
includes taxes & fees
6 Apr - 7 Apr
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Property grounds

3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very good, (6 reviews)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is HK$996
HK$3,574 total
includes taxes & fees
2 Apr - 3 Apr
3BR West Point Retreat-3min to Back Gate+ King Bed
3 bedrooms, desk, iron/ironing board, free WiFi

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is HK$980
HK$3,413 total
includes taxes & fees
2 Apr - 3 Apr
Sleek Escape: Modern 3 BR- 4 Min from West Point !
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chelsea Hotel Reviews

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

10/10 Excellent
"Very clean. Nice room. Noce property "
Tashaun 1-night trip
Posted 10 hours ago
Courtyard by Marriott Poughkeepsie

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?

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9: This holiday home rental outside of Chelsea is located on a lake, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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 Algonquin Park. In the wider area, you’ll find Dutchess Stadium and Benmarl Vineyards and Winery.

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.