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Compare 74 Cottages in Chester with updated reviews, rates, and availability.

Exterior
Historic Cornwall-On-Hudson Cottage w/ Deck!
10.0 out of 10, Exceptional, (8)
"This was our best experience with a VRBO. The posted photos are excellent but, yet the home still exceeded expectations. The hosts were friendly and welcoming. We felt right at home. Great location in Cornwall. We highly recommend and will be staying here again in the future!"
Historic Cornwall-On-Hudson Cottage w/ Deck!
Pool
Cottage at Millpond Falls - A Romantic and Luxurious Escape
10.0 out of 10, Exceptional, (124)
"waterfall and cottage are perfect getaway from the real world. the owners are terrific hosts and provide a wide assortment of amenities"
Cottage at Millpond Falls - A Romantic and Luxurious Escape
Highchair, dining tables
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
10.0 out of 10, Exceptional, (2)
"We came up in the fall to meet friends halfway. The house was so clean and loved all the white sheets and towels. Mostly hardwood or tile in the house. Heat worked great. Huge bath that five kids all got in together and has a blast. Close to warnick which was cute. We did vineyards and farm activities. Lots of foliage. Close to the lake. Would go back for sure!"
NEW Spacious 5 bedrooms with Private Lake & Beach Access and Kayak!
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Property grounds
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
10.0 out of 10, Exceptional, (2)
"We loved our weekend in Beacon. This small, charming rental was very clean and updated. The outdoor space made it feel bigger and you can’t beat the location. We highly recommend staying here and we woulld definitely come back!"
Charming tiny home in delightful Beacon, 2 blocks from main st. Private patio
TV, fireplace, books
Dreamy Hudson Valley Cottage w/ State Park Views
10.0 out of 10, Exceptional, (3)
"The house was perfect for our weekend getaway. Property was exactly as shown in pictures. The house was beautiful and clean. We enjoyed our stay and definitely recommend to everyone."
Dreamy Hudson Valley Cottage w/ State Park Views
Interior
Dreamy Hudson Valley Cottage w/ State Park Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Interior
Warwick Vacation Rental w/ Private Yard & Fire Pit
3.0 star property
10.0 out of 10, Exceptional, (1)
"I was relieved to find that the property looks just like and even better than the pictures online. "
Warwick Vacation Rental w/ Private Yard & Fire Pit
Fridge, oven, stovetop, coffee/tea maker
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!"
Charming Cottage in the Heart of the Shawangunks
Outdoor pool
Mountain House Escape - 1 Hour from NYC
10.0 out of 10, Exceptional, (2)
"Amazing and perfect home for our Thanksgiving stay. Adam was very accommodating and the kitchen was fully equipped for cooking a thanksgiving meal for 10 of us. I would highly recommend this home."
Mountain House Escape - 1 Hour from NYC
Fridge, microwave, oven, stovetop
The Carriage House-Cozy Hide-Away near West Point
10.0 out of 10, Exceptional, (1)
"This wonderful cottage has every amenity a traveler could want.. A beautiful modern kitchen, electric fireplace, lots of LED lighting, ample seating, extremely comfortable bed/pillows, and a huge smart tv. The neighborhood is gorgeous, and the property is located near many places worth visiting. Bear Mountain State Park, and the Storm King Art Center, just to name a few. We loved every minute we spent there. Catherine was a wonderful host who was always available to answer questions. We would...
The Carriage House-Cozy Hide-Away near West Point
Fridge, microwave, stovetop, coffee/tea maker
Putnam Valley Vacation Rental: Patio & Lake Views!
9.8 out of 10, Exceptional, (7)
"Nuery was attentive and wonderful! Thank you for your thoughtful flowers. The listing could have been more descriptive regarding the separation between the large bedroom and full bath from the rest of the house. Too many air fresheners! The kitchen is dark, needs brighter light bulbs. Those are my suggestions. Otherwise the house is gorgeous and it was a great place to stay!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"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 $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Lake
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
9.8 out of 10, Exceptional, (91)
"My family was down for the Spartan race weekend. The property is in a perfect location for proximity to the mountain, as well as Beaches and playgrounds for the kids. It comfortably fit four adults and two kids, and the fenced yard was great for the dog. Michael is a thoughtful and responsive owner, and we are looking forward to staying again next time we are down."
Fenced Yard Private Lakes 7 Beaches Huge Fire Pit
Fridge, microwave, oven, stovetop
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
9.8 out of 10, Exceptional, (10)
"This property is a serene location in the Hudson Highlands that has convenience and good proximity to stores & multiple communities in the area. This home had everything we were looking for and was very comfortable for us. Our host was great too!"
Cozy Rustic Getaway w/ HBO, Porch & Grill Near Lake
Smart TV, fireplace
Beautiful Cottage in Hudson Valley w/Pool & Views
9.8 out of 10, Exceptional, (8)
"This house is amazing! Has practically every amenity you'd need. Gorgeous, clean, comfortable, and very inviting. Check-in was a breeze. I can't wait to come back!"
The price is $300
$698 total
includes taxes & fees
Jun 2 - Jun 3
Beautiful Cottage in Hudson Valley w/Pool & Views
Property grounds
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
9.8 out of 10, Exceptional, (7)
"Thank you Ginny we had a lovely stay at your cottage. Was exactly as pictured! Was perfect for a night away. The only feedback we have is there was no body wash/soap or shampoo (but 3 bottles of conditioner) for the shower. And also in the main bedroom, the center support of the bed frame would shift even just getting into and out of bed. We were a little concerned it might give way but it held and mattress was comfortable. Besides those notes we would definitely recommend staying here!"
The price is $165
$316 total
includes taxes & fees
Jun 9 - Jun 10
Relaxing Farm Cottage Escape, 10 Min from LEGOLAND
Property grounds
Cozy Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
9.6 out of 10, Exceptional, (35)
"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 Countryside Cottage with Spa/Fireplace//Enclosed Yard/Fire Pits
Fridge, microwave, oven, stovetop
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
7.8 out of 10, Good, (16)
"This property was perfect for an overnight stay to visit my cadet at West Point. A nice quiet location and a comfortable, spacious cottage."
The price is $189
$365 total
includes taxes & fees
May 23 - May 24
Retreat to Tranquil Cottage 65 Min from NYC - Onsite Parking, Pet-Friendly
Living area
Cozy Haven: A Romantic Retreat in our Tiny House!
7.4 out of 10, Good, (3)
"very good"
The price is $108
$217 total
includes taxes & fees
May 23 - May 24
Cozy Haven: A Romantic Retreat in our Tiny House!
Pool
Luxe 10 guest Cottage Ski/Golf/Fire pit/Lakes/Hike
6.0 out of 10, (4)
"Great location to the golf courses. Clean house with a beautiful fire pit . I Would rent this place again."
The price is $269
$538 total
includes taxes & fees
Jun 3 - Jun 4
Luxe 10 guest Cottage Ski/Golf/Fire pit/Lakes/Hike
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See all available properties in Chester
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 property types in Chester

Property grounds
Lakefront Luxury on Greenwood Lake
10.0 out of 10, Exceptional, (115)
"We spent a much needed relaxing weekend at this location. I can't say enough good things about this property. It was beautifully decorated, perfectly supplied, and very clean. We would rent this property again."
Lakefront Luxury on Greenwood Lake
Property grounds
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (96)
"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 $184
$264 total
includes taxes & fees
May 27 - May 28
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
1 bedroom, desk, iron/ironing board, travel crib
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
9.8 out of 10, Exceptional, (35)
"This is a cozy property in a very rural setting. The host is extremely responsive and very thorough. It is quiet and private. The furniture and bed are very comfortable. The wood burning stove is a pellet stove which provides enough heat to take the edge off. The hot tub could comfortably fit 4 people. The Village of Cold Spring is less than 10 minutes away, as is the Interstate 84 bridge across the Hudson. If you want to make your own food, bring it. There is no grocery store nearby."
Cozy Countryside Barn with Spa/Fireplace/Enclosed YardFire Pits
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.

Chester Cottages information

Number of reviews
374
Accommodation
74 Cottages
Lowest Price
$148
Highest Price
$300

Frequently asked questions

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What is there to do in Chester near my cottage?
Chester has enough sights to keep you entertained for weeks (or months!), beginning with Brotherhood Winery. Mount Peter Ski Area, Palaia Vineyards Winery and Castle Fun Center are other fantastic attractions. If you’re sticking around a while, Applewood Winery and Harness Racing Museum and Hall of Fame will round off your itinerary nicely.

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