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Compare 91 Cottages in Chester with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is AED 617
AED 911 total
includes taxes & fees
24 Mar - 25 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Chestnut - Charming 3-bedroom cottage in wonderful Fishkill!

Charming Cottage in the Heart of the Shawangunks

10.0 out of 10, Exceptional, (7)
"My bridesmaids and I stayed here the night before my wedding and my husband and I the night of my wedding ..it is absolutely beautiful and private just what we wanted! Would definitely stay here again!"
The price is AED 918
AED 1,925 total
includes taxes & fees
30 Mar - 31 Mar
Charming Cottage in the Heart of the Shawangunks

A romantic cottage and artist's retreat looking down over an enchanted lake

9.4 out of 10, Exceptional, (96)
"It was an awesome stay we loved the couple days we got to spend there!!"
A romantic cottage and artist's retreat looking down over an enchanted lake

Hello Small Stone

9.6 out of 10, Exceptional, (4)
"The house has a lot of character and the outdoor areas are really peaceful. The owner just needs to resolve the issue with sulfur in the water because the rotten egg smell is too strong to tolerate."
The price is AED 661
AED 1,102 total
includes taxes & fees
26 Mar - 27 Mar
Hello Small Stone

Historic 1800's Cornwall-On-Hudson Cottage!

10.0 out of 10, Exceptional, (22)
"Best VRBO OUR FAMILY HAS RENTED .ABSOLUTELY PERFECT, THOUGHTFUL AND SUPER CLEAN,"
Historic 1800's Cornwall-On-Hudson Cottage!

Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

9.8 out of 10, Exceptional, (98)
"Great Highland Lakes Cottage! Clean & well stocked kitchen. Be careful going up or down Breakneck Rd. Thus time of year every view is beautiful! We did lots of small road trips taking in the sites and autumnal views!!"
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit

Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

10.0 out of 10, Exceptional, (142)
"Such a beautiful location. The cottage is quant while having all the modern updates. The hosts have carefully left an array of coffee and welcome goodies, including fresh eggs from their ducks. Will be back! "
Cottage at Millpond Falls - Romantic Luxury Escape - Waterfall views in Warwick

This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

9.8 out of 10, Exceptional, (17)
"The cottage was perfect for our weekend trip to visit our son at West Point. A picturesque drive to West Point, the cottage was so cute and was full of thoughtful amenities. Had we had the time to cook, the kitchen was stocked with spices, condiments, and cooking oils to make it easy to do so. The complimentary coffee was perfect as we arrived late and the stores were closed. The host was easy to contact and so kind and thoughtful. We will definitely book again. "
The price is AED 602
AED 1,523 total
includes taxes & fees
9 Apr - 10 Apr
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

Putnam Valley Vacation Rental: Patio & Lake Views!

3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!

Beautiful Cottage in Hudson Valley w/Pool & Views

10.0 out of 10, Exceptional, (11)
"The house was beautifully decorated and furnished well. We enjoyed the large kitchen. The host responded to questions quickly and well. It is a beautiful region. Views were lovely, and roads and driveway were scraped of snow before we had time to think about it. "
The price is AED 915
AED 2,340 total
includes taxes & fees
24 Mar - 25 Mar
Beautiful Cottage in Hudson Valley w/Pool & Views

Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

2.0 star property
8.0 out of 10, Very Good, (2)
"Nice"
The price is AED 918
AED 1,882 total
includes taxes & fees
24 Mar - 25 Mar
Luxe 10 guest Cottage Ski/Golf/Fire Pit/Lakes/Hike

Charming Lake Community Cottage 2BR Retreat Near Mountain Creek

10.0 out of 10, Exceptional, (1)
"We recently stayed here for the first time in order to visit with our new grandbaby nearby. It far exceeded our expectations - absolutely charming, two good sized bedrooms, working fireplace!, lovely living space, clean, clean, clean, parking spot, anything you forgot (toothbrush, etc.) provided, and a free snack basket! We'll be back. Communication with the host was immediate and helpful. Easy check-in and check-out. Ten stars."
Charming Lake Community Cottage 2BR Retreat Near Mountain Creek

Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

9.8 out of 10, Exceptional, (9)
"We had a great stay in this cozy cabin! The beds were comfortable and the views of the farm and deer were beautiful ! Communication with Ginny was quick and she let us adjust our dates of stay when needed. 😊"
The price is AED 606
AED 1,129 total
includes taxes & fees
26 Mar - 27 Mar
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND

Cozy Haven: A Romantic Retreat in our Tiny House!

7.0 out of 10, Good, (9)
"we enjoyed the cozy home it is a nice place to get away"
The price is AED 551
AED 962 total
includes taxes & fees
24 Mar - 25 Mar
Cozy Haven: A Romantic Retreat in our Tiny House!

Mountain House Escape - 1 Hour from NYC

10.0 out of 10, Exceptional, (7)
"We recently had the pleasure of staying at Deer Hill in Warwick, NY, and it truly exceeded our expectations. The property is set on three-acre expanse in a lovely, and ultra-quiet neighborhood. It was an ideal home for our annual family gathering, which includes our 3 adult children, spouses and two young grandchildren. The large in-ground pool was a hit, and was a source of fun and relaxation throughout our stay. The pool has a shallow end and an 8-foot deep end. The spacious great room served...
Mountain House Escape - 1 Hour from NYC

Dreamy Hudson Valley Cottage w/ State Park Views

9.8 out of 10, Exceptional, (12)
"We loved our two nights at this perfect, comfortable cottage in the Garrison woods. Communication with Ashley was terrific, very prompt and welcoming. The house was very clean and we had a great view. Thank you for a great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views

Hickory - Charming 3-bedroom cottage in serene Fishkill!

Hickory - Charming 3-bedroom cottage in serene Fishkill!

Putnam Valley Vacation Rental: Patio & Lake Views!

9.8 out of 10, Exceptional, (12)
"Cozy, clean property. We had everything we needed for a 3-night stay for West Point Family Weekend. Several stores & restaurants conveniently nearby. Host Neury was most accommodating. Incredible views & scenery!!"
Putnam Valley Vacation Rental: Patio & Lake Views!

NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!

10.0 out of 10, Exceptional, (5)
"The house is even more beautiful than the photos. From the spa-like bathrooms, to toys and books for kids, to the little extra amenities like qtips and bandaids, it was the perfect getaway for everyone in our party of all ages."
NEW Spacious 5 bedrooms with Public Lake & Beach Access and Kayak!
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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Other property types in Chester

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

Private Estate 9BR w/Pool, Hot Tub & Scenic Views!

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

9.4 out of 10, Exceptional, (3)
"Plenty of room for my family"
The price is AED 951
AED 1,084 total
includes taxes & fees
24 Mar - 25 Mar
Large Relaxing Family Retreat In The Hudson Valley with Theatre and Gazebo

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is AED 617
AED 911 total
includes taxes & fees
24 Mar - 25 Mar
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.

Frequently asked questions

How much do cottages in Chester cost?
Prices for cottages in Chester range between AED 555 and AED 918 per night. Whatever your budget, you’re sure to find an ideal place to get in tune with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Chester with Expedia?
Booking a cottage in Chester is as simple as deciding on your travel dates and choosing your ideal place for a vacation in nature. From chic retreats to affordable stays and cottages that include conveniences like a kitchen, Expedia has something for all tastes and styles. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Chester?
With Expedia’s useful filter tool, scoring cheap cottages in Chester is a snap. To find properties that’ll make your hip pocket happy, refine your search by amenities, star rating and budget.