Chelsea Vacation Rentals

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Check prices for these dates

Tonight
Dec 19 - Dec 20
Tomorrow
Dec 20 - Dec 21
This weekend
Dec 19 - Dec 21
Next weekend
Dec 26 - Dec 28

Our top choices for Chelsea vacation rentals

Terrace/patio
Wappinger Cottage - Scandinavian retreat on a creek

Wappinger Cottage - Scandinavian retreat on a creek

Wappinger Cottage - Scandinavian retreat on a creek
Poughkeepsie
10.0 out of 10, Exceptional, (24)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek
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

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Fishkill
9.6 out of 10, Exceptional, (50)
"Inside was very nice, outside could use some curb appeal. Enjoyed our stay "
United States
Karen K.
The price is ￥38,489
￥49,524 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo
Interior
Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is ￥56,016
￥73,337 total
includes taxes & fees
Dec 20 - Dec 21
Large,Cozy,Bright Apartment, Business Themed.
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

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, (129)
"It has an incredible mountain and water view. "
United States
MIHYUN
The price is ￥29,236
￥47,323 total
includes taxes & fees
Dec 21 - Dec 22
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Interior
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!

2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Garrison
10.0 out of 10, Exceptional, (14)
"Absolutely amazing stay! Matt was great!!"
United States
Jamie F.
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Exterior
Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!

Rustic Cabin in Fishkill!
Fishkill
10.0 out of 10, Exceptional, (3)
"Ideal cabin getaway. "
United States
Nadja E.
The price is ￥47,042
￥70,823 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Rustic Cabin in Fishkill!
1 bedroom, desk, iron/ironing board, WiFi
Mountain View escape

Mountain View escape

Mountain View escape
New Paltz
10.0 out of 10, Exceptional, (70)
"Really cute cottage with a view of Skytop and the mountains. Quiet location. Fully equipped kitchen. Enjoyed our stay very much. "
United States
barbara d.
Mountain View escape
Interior
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (11)
"Enjoyed the stay. Nice place to relax for a weekend."
United States
Marie J.
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Exterior
Hickory on Willow Lake

Hickory on Willow Lake

Hickory on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (5)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
United States
Rachel C.
The price is ￥59,906
￥86,266 total
includes taxes & fees
Dec 29 - Dec 30
Hickory on Willow Lake
Property grounds
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.

Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
3.0 star property
Carmel
10.0 out of 10, Exceptional, (3)
"It was great! We loved staying in this cute house. Proximity to the lake is great, and the backyard is quite beautiful."
United States
Varuna S.
The price is ￥18,467
￥39,226 total
includes taxes & fees
Dec 21 - Dec 22
Cozy cabin with deck and fireplace steps from White Pond Lake. Dog friendly.
Terrace/patio
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!

Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Holmes
10.0 out of 10, Exceptional, (197)
"Great place to get away. Absolutely recommend it. "
United States
Demian B.
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC! No Pet Fees!
Dining
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Monroe
6.8 out of 10, (5)
"It was a great home with lots of space indoor and outside. "
United States
Yogita R.
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Interior
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY

Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Poughkeepsie
10.0 out of 10, Exceptional, (2)
"Great host"
United States
Lindsey F.
The price is ￥33,610
￥100,235 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Stunning 5-bedroom house with AC / Heat in charming Poughkeepsie NY
Outdoor spa tub
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
2.0 star property
New Paltz
9.4 out of 10, Exceptional, (24)
"Beautiful comfortable, clean "
United States
Michal G.
The price is ￥24,493
￥50,202 total
includes taxes & fees
Dec 22 - Dec 23
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Exterior
Chestnut on Willow Lake

Chestnut on Willow Lake

Chestnut on Willow Lake
Fishkill
9.6 out of 10, Exceptional, (4)
"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 ￥76,977
￥109,496 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Chestnut on Willow Lake
Apartment (1 Bedroom) | Front of property
Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex

Explore & Work! Stylish Washington Heights Duplex
3.0 star property
Newburgh
Explore & Work! Stylish Washington Heights Duplex
Property grounds
Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!

Red Cottage - Lakeside Property!
Fishkill
The price is ￥81,254
￥114,922 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Red Cottage - Lakeside Property!
Terrace/patio
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Newburgh
10.0 out of 10, Exceptional, (22)
"Great host, amazing area, perfect get away!"
United States
Gianna W.
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

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

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
new paltz
9.4 out of 10, Exceptional, (6)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is ￥27,992
￥110,425 total
includes taxes & fees
Dec 20 - Dec 21
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (66)
"Such a cute place to stay"
United States
Melissa
The price is ￥27,214
￥50,334 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy country efficiency in the Hudson Valley
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

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

10/10 Excellent
"Very clean. Friendly staff. Breakfast was excellent. Room was great. What a surprise that Santa was there for breakfast. Would definitely go back."
Christine 1-night trip
Posted 3 days ago
Hampton Inn & Suites 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 vacation rental in Chelsea?

Yes, we have vacation rentals near the most popular points of interest in Chelsea, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Chelsea has to offer?

Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo: This vacation home rental outside of Chelsea offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with an oven, a microwave, and kitchenware, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 larger area, you’ll find Benmarl Vineyards and Winery and Dia Beacon.

What are vacation rentals like in Chelsea?

Vacation rentals are private accommodations you can book for several days or more in Chelsea. Vacation rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family trips or small group gatherings.