Chelsea Holiday Rentals

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Holiday Rentals in Chelsea

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, 96 reviews
"Comfortable apartment with a phenomenal view! The space could use a deep clean and some decluttering, but that view!!! Did I mention that the view was A-mazing?!?"
The price is NZ$469
per night
24 Jun - 25 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
10.0 out of 10, Exceptional, 39 reviews
"Private bath, 1 BR + kitchen, what more could one ask for. Great view of the trees and river from balcony, and double rainbow to boot. Easy check in. Host was very responsive."
Hudson River View Suite-idyllic getaway with fireplace & private deck-75 min NYC
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
9.8 out of 10, Exceptional, 24 reviews
"The backyard was really cool! Great features. Beautiful, peaceful, and private. We did not see or hear anyone else on the property during our stay. The apartment was very nice. Cozy, clean and comfortable, perfect for two. The host, Ryan was extremely responsive and friendly. We had an amazing stay would definitely recommend!"
The price is NZ$465
per night
21 Jun - 22 Jun
Enjoy a cozy, quiet spot off the main roads but close to hiking/biking trails!
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Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
9.0 out of 10, Wonderful, 30 reviews
"Very charming one room apartment with bathroom and kitchen area. Beautiful surrounding you with very pleasant hosts"
Studio near Millbrook, Poughkeepsie. Close to Polo Club w/ mini farm!
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
9.6 out of 10, Exceptional, 35 reviews
"Three nights here as we toured the area. Check in was easy. We were able to access the VRBO app 30 minutes prior to our arrival. By the time we reached the driveway, Ruben had sent the access code.The road to the house is gravel and only wide enough for one car. We were glad we had arrived during the day.The house has an antique store vibe. Lots of books for a rainy day activity. FYI, the photos on the listing are a bit different from what we saw in the rooms. The dining table is larger with...
Cozy Country Cottage with Basketball Court/Spa/Fireplace/Enclosed Yard/Fire Pit
Spectacular Log Home Estate North Wing Apt
10.0 out of 10, Exceptional, 25 reviews
"All as represented. Had everything we needed for a lovely home away from home!"
Spectacular Log Home Estate North Wing Apt
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, 63 reviews
"Stayed for West Point graduation. Beautiful home, scenic views, and everything we needed."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, 38 reviews
"My husband and I greatly enjoyed our stay! We mentioned that we were traveling for our honeymoon and upon our arrival, the host had left a bottle of wine and some little decorations on the dining room table to celebrate our marriage! It was so thoughtful and sweet!! The Vrbo itself was cozy and tidy. We enjoyed cooking in the kitchen and listening to the music of Motown on the cd player. Our host was prompt to respond to messages and answered all questions clearly. We loved staying close to so...
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
10.0 out of 10, Exceptional, 171 reviews
"We would 100% go back to this house. The cabin was immaculate and had all the essential equipment for very successful fishing. We went with a family of four and the cabin was perfectly sized. The host was responsive and attentive. I have no critiques as we had an absolute blast."
Log Cabin On A Lake With Private Dock & Beach! One Hour from NYC!
Sweet and spacious mountain view home w/fireplace!
9.8 out of 10, Exceptional, 14 reviews
"Sweet space, well-stocked and nice open living and kitchen area. We enjoyed watching birds eat from the bird feeders and a family of deer graze in the meadow and along the edge of the woods! The location was situated well for accessing nearby hiking and is not far from scenic Hudson landmarks. Excellent quiet place to relax and take things at your own pace."
The price is NZ$651
per night
20 Jun - 21 Jun
Sweet and spacious mountain view home w/fireplace!
Spacious restored Victorian w/ wraparound porch
9.4 out of 10, Exceptional, 10 reviews
"The property was gorgeous, the house large enough to accommodate our group. The kitchen was well stocked. We used the pool, hot tub, fire pit, and pool table. The indoor and outdoor speakers were a nice touch. I would definitely recommend this home I had to reach out to our host 2 days before check in to find out how to get in- usually that is communicated earlier than that. I had informed the host that we were going to have a luncheon for 10 additional people after the memorial service and was...
Spacious restored Victorian w/ wraparound porch
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
9.6 out of 10, Exceptional, 30 reviews
"This place is wonderful!!!! It was a beautiful stay."
The price is NZ$611
per night
24 Jun - 25 Jun
Luxury Waterfront Retreat near New Paltz & the Gunks: Hike, Bike, or Relax!
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
10.0 out of 10, Exceptional, 35 reviews
"I needed a place in Wallkill NY to stay. This VRBO was perfect!"
The price is NZ$354
per night
20 Jun - 21 Jun
Create Memories at our Modern Waterfront 1 BR Apartment: Hike, Sip Wine, Relax!
Cozy country efficiency in the Hudson Valley
9.8 out of 10, Exceptional, 42 reviews
"We spent a wonderful night at this apartment. The space is so comfortable and peaceful. It is next to the owners' home but very private and extremely quiet. The neighborhood is a dead end and has few cars. The apartment feels sizable and is well laid out. It was clean and well stocked. The owners were very responsive when we had a question. We would absolutely come back!"
The price is NZ$353
per night
8 Jul - 9 Jul
Cozy country efficiency in the Hudson Valley
Renovated 1850's Cottage on Storm King Mountain
9.8 out of 10, Exceptional, 8 reviews
"It was a beautiful setting with water fall. The home itself needs a little work. It is well used and needs some TLC. Photos look much better then actual home."
Renovated 1850's Cottage on Storm King Mountain
Hudson Valley Newburgh -Remodel Lrg Apt
5.0 out of 10, 2 reviews
"The pictures in this listing completely misrepresented the neighborhood. We only spent about an hour in the VRBO but didn't feel safe there for several reasons. First of all, the room wasn't secure because it was opened up to the neighborhood through the upper floor that let out to the fire escape. Second of all there were large groups of people in the streets having block parties that made us feel like our rental car wasn't safe from vandalism or burglary. The last straw was when we talked to a...
Hudson Valley Newburgh -Remodel Lrg Apt
Cabin in the heart of the Hudson Valley, Cabin 2
9.4 out of 10, Exceptional, 3 reviews
"Great tiny house for a stay upstate. Check in was easy and the place is clean!"
The price is NZ$266
per night
20 Jun - 21 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
9.0 out of 10, Wonderful, 22 reviews
"This house has an ideal location to see lots of local sites of interest in the Hyde Park and Poughkeepsie area. Easy trip from there to West Point, Hyde Park and the Culinary Institute from the location, and great restaurant, Tiramasu, is very close. The house is immaculate! The beds were very comfortable, linens were provided, the bathrooms were spacious and the five of us had plenty of room for our toiletries. The house has steps to its multiple levels for all essential rooms, not accessible....
1 HR NYC Getaway Awesome Newly Renovated Home on 4 Acres, Stunning Views
Kick back & relax in this peaceful, stylish place to stay with the whole family.
10.0 out of 10, Exceptional, 12 reviews
"Beautiful property, plenty of room! Clean, plenty of linens and other amenities As described. Would definitely recommend if needed for large family/friends to attend events in this area."
Kick back & relax in this peaceful, stylish place to stay with the whole family.
Private room in a single family house near Peekskill
9.8 out of 10, Exceptional, 13 reviews
"My wife and I enjoyed our stay. Property owner was very responsive to questions. Home was very clean and inviting. We loved the cats!"
The price is NZ$233
per night
26 Jun - 27 Jun
Private room in a single family house near Peekskill
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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.

Other types of properties in Chelsea you may be interested in

HYATT house Fishkill/Poughkeepsie
3.0 star property
8.6 out of 10, Excellent, 1,000 reviews
"They have a little bit of everything, including an indoor heated pool, a hot tub, laundry, a fitness center, and a full breakfast as opposed to those with a continental breakfast. The staff is very friendly, and the rooms as very comfortable."
The price is NZ$261
per night
24 Jun - 25 Jun
HYATT house Fishkill/Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4.0 star property
8.2 out of 10, Very good, 983 reviews
"Nice staff and beautiful room "
The price is NZ$241
per night
9 Jul - 10 Jul
DoubleTree by Hilton Poughkeepsie
Overlook Lodge at Bear Mountain
2.5 star property
8.0 out of 10, Very good, 1,002 reviews
"Cool area but this facility needs updating."
The price is NZ$250
per night
27 Jun - 28 Jun
Overlook Lodge at Bear Mountain
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chelsea holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chelsea. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chelsea. Seeing all the best attractions is bound to make you fall in love with Chelsea. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chelsea short-term rentals, that won’t be hard to do.

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 Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits: This holiday home rental outside of Chelsea is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 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.

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