
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
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Other great vacation rentals in Chester
Guest favorite

Home in New Windsor
4.91 out of 5 average rating, 121 reviewsView House
JamieRating, 5 stars1 week ago
A fantastic stay: totally private yet with expansive views. Birds galore, June was the perfect time to spot them all. House is gorgeous and unique. Fantastic hosts, stayed here 8 years ago and I very much hope to be back before another 8 years passes. Thank you to Lisa and Nafeeza!
Superhost

Apartment in Goshen
4.84 out of 5 average rating, 62 reviewsPrivate 1 bedroom apartment Village of Goshen
BrittneyRating, 5 stars3 weeks ago
We had a great stay at Marty’s place! We were in town for a wedding and it was the perfect accommodation for a long weekend, especially if you love historic architecture and peaceful surroundings. Walkable to breakfast and lunch spots which was a plus! Very friendly and helpful host as well. Would definitely recommend!

Place to stay in Goshen
4.7 out of 5 average rating, 89 reviewsGroovy Digs for a unique stay on Murray Hill
JayleeRating, 5 stars1 month ago
Very glad I found Groovy Digs!! Loved the decor and how well put the together the host has the place. Great neighborhood with many things to do nearby. Would definitely recommend this place to others :) We hope to back again!
Guest favorite

Cabin in Greenwood Lake
4.99 out of 5 average rating, 90 reviewsModern Nordic Designed Cabin
FeRating, 5 stars2 weeks ago
The Nordic Cabin was the perfect setting for my husband and I to celebrate our 22nd wedding anniversary. The cabin is beautiful and the modern design, furnishings, and decor really stand out. Instructions of how to get into the cabin and the pitcures provided made check in and check out a breeze. The kitchen was well stocked. A bottle of white wine and a few treats were left for us. The kitchen offered different spices, oils, milk, and eggs. Kitchen utensils, pots/pans, dishes, cups, glasses, etc are provided, as well as cleaning supplies. The bathroom was stocked with toiletries. We spent a lot of time relaxing in the cozy living room and slept well in the beautiful bedroom. Last, I have to say that the first time we opened the gate at night, after dinner in Warwick, and saw all of the outdoor lights on, really made it feel like we were entering an enchanted garden. Would definitely come back!! Thank you Kamil and Margaret!!
Guest favorite

Apartment in Chester
4.82 out of 5 average rating, 17 reviews“The Loaf” in Sugar Loaf NY
ElizabethRating, 5 stars3 weeks ago
We planned a trip to Legoland for my son’s birthday and discovered this place was only 10 min away! I grew up visiting Sugar Loaf and it was just as quiet, peaceful and beautiful as I remembered. This place was way more unique and spacious than I expected. Really cool layout, super cozy, everything we could possibly need and more. It was just such a special spot. The host made some dinner recommendations and we had so much fun going out to the Tap House across the street! Such a fun vibe and great food and service. We loved strolling around and coming back to this spot to crash. Beds are super comfy, lots of room, so much character. I wish we could’ve explored Sugar Loaf more but it was a short getaway and we had a great day at Legoland which was such a quick ride. If you visit be sure to visit The Candle Shop. The owner Peter was one in a million. Next time we’ll account for extra time to check out the amazing local businesses. What a special, memorable weekend away. We’ll be back!
Guest favorite

Home in Greenwood Lake
5 out of 5 average rating, 23 reviewsLakeview House ~ Hot Tub, Firepit, Stunning Views
ScottRating, 5 stars5 days ago
The home was pristine and beautifully designed, feeling like a brand new home. Everything was purposely placed to have exactly what you would think you’d need. The host is extremely friendly and super responsive. The views of the lake are awesome. The bedrooms are huge and the beds and bedding are extremely cozy (we all slept like babies). The duel decks are a really cool set up with the hot tub on the bottom such a cool vibe with really nice ceiling lights hanging. We came for a work escape as a team, and this was a great stay for us. The bedrooms upstairs also had their own little balconies, which is great to enjoy a morning cup of coffee before getting our day started. They also had all the amenities in the kitchen you could ever need.
Top guest favorite

Home in Chester
5 out of 5 average rating, 9 reviews4 Bedroom Home with Hot-Tub
corrineRating, 5 stars1 week ago
The house is fantastic and had everything we needed for a family filled weekend. Spacious, clean and tons of amenities. We didn’t get to use the pool because it was cold, but it was very clean and inviting. We would definitely return.
Superhost

Home in Chester
4.83 out of 5 average rating, 23 reviews6 bedroom nice big colonial house
KnoxRating, 5 stars1 month ago
Fantastic home, stayed twice and worked great for a team dinner both times. Love the place and although I’m leaving the area would stay again!
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- United Nations Headquarters
- Bethel Woods Center for the Arts
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo
- The Metropolitan Museum of Art
- Bushkill Falls
- Astoria Park