Chelsea Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Chelsea holiday rentals

Interior

Updated Home w/ Patio Half Mile to West Point

Updated Home w/ Patio Half Mile to West Point
3.0 star property
Highland Falls
The price is HK$1,919
HK$4,869 total
includes taxes & fees
2 Jun - 3 Jun
Updated Home w/ Patio Half Mile to West Point
Exterior detail

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days

Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
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$1,407
HK$3,907 total
includes taxes & fees
18 May - 19 May
Walk-to-Lake Cottage With Paddleboards for Peaceful Summer Days
Exterior

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4 reviews)
"We really enjoyed the privacy of the grounds, lake, dock , swimming, boats and paddle boards. The kitchen was well equipped and the beds were comfy. We had a great stay, thanks."
United States
Doria W.
The price is HK$3,876
HK$5,537 total
includes taxes & fees
18 May - 19 May
Chestnut on Willow Lake
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)
"Beautiful house. Great location and awesome hosts!"
United States
Robert T.
The price is HK$1,586
HK$3,085 total
includes taxes & fees
21 May - 22 May
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.
Fridge, microwave, oven, stovetop

River Views & Hot Tub | Riverview on Washington

River Views & Hot Tub | Riverview on Washington
Newburgh
The price is HK$2,960
HK$6,818 total
includes taxes & fees
18 May - 19 May
River Views & Hot Tub | Riverview on Washington
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, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is HK$1,551
HK$2,590 total
includes taxes & fees
18 May - 19 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
7 bedrooms

Ready for Summer West Point - Jacuzzi Pool Games

Ready for Summer West Point - Jacuzzi Pool Games
2.0 star property
Cornwall
The price is HK$5,724
HK$11,127 total
includes taxes & fees
19 May - 20 May
Ready for Summer West Point - Jacuzzi Pool Games
Private kitchen

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, (1 review)
"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$1,480
HK$1,905 total
includes taxes & fees
24 May - 25 May
2-bedroom apartment in excellent Newburgh with AC and charm
Exterior

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, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is HK$1,323
HK$2,202 total
includes taxes & fees
18 May - 19 May
Cabin in the heart of the Hudson Valley, Cabin 3
Fridge, microwave, oven, stovetop

Contemporary Cozy Cottage

Contemporary Cozy Cottage
Lake Peekskill
9.8 out of 10, Exceptional, (34 reviews)
"Very clean comfortable quiet place"
United States
Mauro C.
The price is HK$1,762
HK$3,287 total
includes taxes & fees
31 May - 1 Jun
Contemporary Cozy Cottage
Exterior

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3 reviews)
"Ideal cabin getaway. "
United States
Nadja E.
The price is HK$2,369
HK$3,549 total
includes taxes & fees
18 May - 19 May
Rustic Cabin in Fishkill!
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
9.2 out of 10, Wonderful, (65 reviews)
"Great spot! Very unique, has lots of charm!"
United States
Brian
The price is HK$1,938
HK$2,549 total
includes taxes & fees
19 May - 20 May
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
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)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is HK$1,323
HK$2,202 total
includes taxes & fees
18 May - 19 May
Cabin in the Heart of the Hudson Valley, Cabin 1
Property grounds

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (8 reviews)
"We had a great time staying here. It was very clean and the view was amazing. Wanted to meet up with some family and it was perfect for relaxing and catching up. Host accommodated our early check in request and was available during our stay when we had minor questions. Overall, it was wonderful."
United States
Joe K.
The price is HK$1,770
HK$3,459 total
includes taxes & fees
31 May - 1 Jun
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Interior

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
Large,Cozy,Bright Apartment, Business Themed.
Fridge, microwave, oven, stovetop

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
8.6 out of 10, Excellent, (7 reviews)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
The price is HK$1,762
HK$6,017 total
includes taxes & fees
18 May - 19 May
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Property grounds

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is HK$4,092
HK$5,639 total
includes taxes & fees
18 May - 19 May
Red Cottage - Lakeside Property!
Iron/ironing board, WiFi, bed sheets

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC

Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Carmel Hamlet
The price is HK$1,142
HK$1,594 total
includes taxes & fees
18 May - 19 May
Spacious 4-bedroom estate in adorable Carmel Hamlet with AC
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.4 out of 10, Exceptional, (6 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is HK$2,064
HK$3,471 total
includes taxes & fees
1 Jun - 2 Jun
Fabulous 3bdrm Home w/parking!
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)
"Space was excellent, the multiple bedrooms with the extra bathroom was great. Kitchen was stocked with utensils, bathrooms were clean, living space was comfortable and cozy."
United States
Christine T.
The price is HK$1,958
HK$4,793 total
includes taxes & fees
19 May - 20 May
3BR West Point Retreat-3min to Back Gate+ King Bed
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

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

10/10 Excellent
"The food and the service was a 20 out 10 highly recommend. We had a graduation dinner there and every food item was fresh, delicious and fingerlicking good."
Sharon 2-night trip
Posted 1 hour ago
DoubleTree by Hilton Poughkeepsie Convention Center

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:

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  • 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?

1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views: This holiday home rental outside of Chelsea is located in the mountains, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 4 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 Dia Beacon and Mount Saint Mary's College Newburgh.

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.