Chelsea Holiday Rentals

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Holiday Rentals in Chelsea

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

9.8 out of 10, Exceptional, (7)
"Great spot, wonderful host. Would recommend to anyone!"
The price is AU$618
includes taxes & fees
16 July - 17 July
Lux Bungalow on Gorgeous Lake. Relax. Explore nearby towns. Ski. Kayak. Hike.

Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

10.0 out of 10, Exceptional, (15)
"We had a great stay and had everything we needed!"
The price is AU$1,340
includes taxes & fees
13 July - 14 July
Beautiful Escape! Hudson Valley LakeHouse. 90min from NYC & 30min from Beacon.

3-bedroom and 2 bath cottage across Waterfall

The price is AU$737
includes taxes & fees
1 Aug - 2 Aug
3-bedroom and 2 bath cottage across Waterfall

Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

9.0 out of 10, Wonderful, (9)
"Truly a hidden gem. The property and home were nothing short of extraordinary. For those looking for a great location with access to hiking and a one of a kind experience this is the place."
The price is AU$404
includes taxes & fees
13 July - 14 July
Cozy 1845 Chapel Escape near Appalachian Trail and Fahnestock Park

Contemporary Cozy Cottage

10.0 out of 10, Exceptional, (23)
"Our stay was lovely. Nadia was a wonderful host and the property was so welcoming."
The price is AU$658
includes taxes & fees
13 July - 14 July
Contemporary Cozy Cottage

Rustic Cabin in Fishkill!

10.0 out of 10, Exceptional, (1)
"Beautiful property with many different areas to explore. We originally intended to spend more time in beacon but decided it was more fun hanging out here. "
The price is AU$644
includes taxes & fees
17 July - 18 July
Rustic Cabin in Fishkill!

Chestnut on Willow Lake

9.0 out of 10, Wonderful, (2)
"We absolutely loved our stay in Chestnut—the home was spotless and comfortable, the property was terrific (the lake was perfect for swimming, boating, and fishing), and the owners/management were all very friendly and helpful. We definitely plan to return!"
The price is AU$893
includes taxes & fees
17 July - 18 July
Chestnut on Willow Lake

Hickory on Willow Lake

9.0 out of 10, Wonderful, (2)
"Cute cottage on nice grounds with a small lake. Kayaks and life jackets available for use was a big plus"
The price is AU$943
includes taxes & fees
17 July - 18 July
Hickory on Willow Lake

Red Cottage - Lakeside Property!

The price is AU$905
includes taxes & fees
17 July - 18 July
Red Cottage - Lakeside Property!

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Charming 2-bedroom Guest Suite with Pool Access and Fitness Room

Spacious New Luxurious holiday house in lovely Hudson Valley

10.0 out of 10, Exceptional, (11)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is AU$1,186
includes taxes & fees
14 July - 15 July
Spacious New Luxurious holiday house in lovely Hudson Valley

Historic Hudson Valley Estate

The price is AU$2,397
includes taxes & fees
14 July - 15 July
Historic Hudson Valley Estate

Modern Converted Barn with Hot Tub!

10.0 out of 10, Exceptional, (4)
"The house has a big open floor plan with extra large windows letting light and views in. The bedrooms are comfortable and the kitchen is well equipped. Big playroom was heaven for our toddler. Highly recommend.this property."
The price is AU$1,328
includes taxes & fees
14 July - 15 July
Modern Converted Barn with Hot Tub!

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

9.8 out of 10, Exceptional, (22)
"Communication was easy, location and parking was great! Very clean and cozy!"
The price is AU$505
includes taxes & fees
20 July - 21 July
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

West Point Family Retreat, 5 min walk to Thayer!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Nice houseAwesome kitchen Granddaughter loved the bunk bed and the many games"
The price is AU$1,279
includes taxes & fees
13 July - 14 July
West Point Family Retreat, 5 min walk to Thayer!

Lovely 3BR Home with parking-Walk to WP Gate!

10.0 out of 10, Exceptional, (4)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
The price is AU$520
includes taxes & fees
29 July - 30 July
Lovely 3BR Home with parking-Walk to WP Gate!

Fabulous 3bdrm Home w/parking!

6.0 out of 10, (1)
"The proximity to Westpoint was great. Trashy neighborhood. Very loud construction early in the morning. The cooking supplies were limited and one of the handles on the pans fell off while we were there. It was okay, but probably wouldn't return."
The price is AU$546
includes taxes & fees
4 Aug - 5 Aug
Fabulous 3bdrm Home w/parking!

Room for Everyone: Spacious 6BR West Point Retreat

10.0 out of 10, Exceptional, (1)
"Great location for Westpoint visit. As described. Clean with new updates. "
The price is AU$1,732
includes taxes & fees
17 July - 18 July
Room for Everyone: Spacious 6BR West Point Retreat

Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

10.0 out of 10, Exceptional, (4)
"Our stay was only a couple nights but it was what we expected. I would recommend this property. Had a great stay."
The price is AU$967
includes taxes & fees
30 July - 31 July
Beautiful, Spacious, 5 Acre Hudson Valley Family Retreat

Cozy Escape -Strong Wi-Fi -Prime Location

7.4 out of 10, Good, (3)
"The property was perfect for our little weekend getaway. It was very clean and cozy and the host Christina made it so easy for check in and was available for any questions. We would definitely stay again."
The price is AU$555
includes taxes & fees
17 July - 18 July
Cozy Escape -Strong Wi-Fi -Prime Location
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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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 Fishkill Ridge. 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.