Vacation rentals in Chester

5 out of 5 average rating, 121 reviews

Home in Greenwood Lake

Escape to the lake!LAKEFRONT/Hot-tub/1 hour to NYC

LauraRating, 5 stars1 week ago

Our stay at Starlight Serene was everything we hoped it would be! John was very responsive and helpful, especially as this was our first time using AirBnB. The pictures are very accurate, there were plenty of towels, linens, and a VERY well equipped kitchen - much more than we expected (or I have in my own house, I think!). Lots of nice bonuses to this place - my kids loved the firepit and there was wood on hand as well as a s'mores kit; the hot tub was warm and ready when we arrived. You are at the narrower end of the lake, but still a beautiful view with plenty of wildlife. The location is great - roughly 30ish minutes to Bear Mountain, Legoland, and the Palisades Center (which had tons of rainy-day fun for kids). We even rented a pontoon boat from Murphy's Cove Marina - Richie was really wonderful to us and our kids and they loved their first time boating and fishing on the lake. Thanks for a great experience John!

4.87 out of 5 average rating, 129 reviews

Home in Lake Ariel

Lakeview Chalet - Pool & Lake/Beach - Kayaking

Luz AngelaRating, 5 stars3 months ago

Great deck and view of the lake - peaceful and relaxing. The house had all the amenities we needed - great grill, large sitting area and TV to hang out with family. The kids enjoyed playing in the downstairs area and roasting marshmallows out back.

4.92 out of 5 average rating, 470 reviews

A spacious wooden deck features a seating area with cozy chairs, a dining table, and an umbrella for shade. Potted plants adorn the space, and a grill is positioned nearby, creating an inviting area for outdoor gatherings.

Home in Woodstock

Mountain View Cottage - Sauna, Jacuzzi, Fire Place

NiharRating, 5 stars2 weeks ago

fantastic host and super helpful whenever we had questions. my wife left her iPad there and they mailed it back. verry appreciative of that. first time using a wood fired sauna- I was skittish at first, but it was a great amenity. hot tub was clean and worked well as well. would definitely recommend if you're eyeing a rustic retreat.

Cottage in Livingston Manor

4.99 out of 5 average rating, 146 reviews

Cozy mountain top home - views, 5acres & a gym.

NikhilRating, 5 stars2 weeks ago

The cottage was lovely and very comfortable. Simon left us detailed instructions and we had no issues in finding it and settling in. As the weather took a turn for the worse, we spent most of a day cozy in the house. Our dogs were also very comfortable and loved the large backyard. The house decor is very tastefully done, and not only looks great but looks like special effort has been taken to make everything comfortable and easy to use. Thank you for sharing your home!!

4.97 out of 5 average rating, 135 reviews

Home in Bushkill

Sweet Home Poconos

SRating, 5 stars2 months ago

We had a terrific time. It’s a lovely home- 20 min from Shawnee mountain and steps away from an indoor/outdoor pool facility (depends on weather), sledding hill and small skiing hill with ski lift. I would absolutely stay here again- and highly recommend for anyone with young kids looking to teach them to ski. Very very convenient. The hosts were available for questions and were friendly/flexible. Incredible customer service. We will be back!

4.96 out of 5 average rating, 264 reviews

An inviting living area features a spacious sectional sofa positioned beside a wooden coffee table. Natural light floods through large windows, illuminating the rustic wood accents and modern appliances in the kitchen area. A staircase leads to the upper level.

Home in Greentown

Brand new one bedroom paradise

JaisonRating, 5 stars1 week ago

Adriana, the epitome of hospitality, meticulously attended to every detail, ensuring our comfort and safety from the moment we arrived. Her recommendations were impeccable, and the accommodations were simply exquisite. My wife and I savored the local cuisine and found solace in the tranquility of this secluded lovers cottage.

4.92 out of 5 average rating, 140 reviews

A serene lake view is presented, showcasing calm waters bordered by lush greenery and residential homes on the opposite shore. A private dock is visible in the foreground, accompanied by a shaded gazebo. The bright blue sky reflects on the lake's surface.

Home in Hopatcong

Lakefront Hopatcong w/dock kayaks fishing near NYC

AmandaRating, 5 stars4 days ago

Had an amazing stay at this beautiful property. It was spacious, clean, and had everything we needed. The host was responsive and super helpful with everything. The views and location were truly incredible. I recommend this house to anyone who is looking to stay in this area.

Vacation rentals for every style

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Popular amenities for Chester vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chester's top sights

Tin Barn Brewing33 locals recommend

Sugar Loaf Performing Arts Center24 locals recommend

Rushing Duck Brewing21 locals recommend

Allan's Falafel20 locals recommend

Christopher's Bistro19 locals recommend

Sugar Loaf Taphouse18 locals recommend

Other great vacation rentals in Chester

4.97 out of 5 average rating, 182 reviews

An outdoor deck area is shown featuring several light-colored Adirondack chairs arranged around a stone fire pit. A neatly stacked pile of firewood is positioned against a backdrop of trees, creating a natural setting for relaxation and gatherings.

Home in Millerton

Vacation Home In Millerton

BettyRating, 5 stars1 week ago

We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!

5 out of 5 average rating, 14 reviews

A spacious living area features a comfortable sectional couch, complemented by a sleek coffee table. Vaulted wooden ceilings enhance the open feel, while large windows provide views of the lush outdoor scenery. A decorative fireplace adds a cozy touch, flanked by a potted plant and wall art.

Home in South Fallsburg

Renovated & Spacious 3BR Catskills Retreat

NicolaRating, 5 stars1 month ago

Alan was a pleasure to work with. He promptly answers all my messages. We worked with him for our company stays. we stayed well over a month in 2 of his home. Check out all his homes for rent.

4.92 out of 5 average rating, 39 reviews

A lakeside scene features a small fire pit surrounded by four chairs on grassy ground. Two kayaks are visible near a wooden dock extending into the lake, which reflects the overcast sky. Lush trees line the distant shore.

Apartment in Cochecton

Lake view with new 6 person jacuzzi & lake area

JaneRating, 5 stars1 month ago

I was looking for some quiet after a stressful few months and something of a view. I love the water so I picked this place and it want a far drive from me. I felt at home and comfortable. The kitchen has everything you could think of which was great because I really wanted to bake for myself and just do a great self care weekend which I did. Me and my pup got to have some alone time and hang by the water across the street at the gated off little beach. Hung out in the hammock and sat on the boat launch. Exactly what I needed. Definitely coming back !

4.93 out of 5 average rating, 124 reviews

Home in Lakeville

The Great Escape

CristhianRating, 5 stars3 months ago

Great place. House is lovely, clean and peaceful.

4.73 out of 5 average rating, 111 reviews

The entrance of Minerals Resort and Spa is showcased, featuring a prominent sign surrounded by vibrant autumn foliage and colorful flower beds. The building's stone accents and unique architecture complement the natural scenery of the lush mountains in the background.

Condo in Vernon Township

200 yds Minerals - great for hotel weddings

SaraRating, 5 stars5 months ago

We had a great time! The unit is an easy walk to Minerals, and the layout was perfect for our needs. Joann was a fantastic host and we can’t wait to stay again!

4.85 out of 5 average rating, 27 reviews

The home is set within a wooded landscape, featuring a large wrap-around deck and distinctive red accents. The multi-level structure includes large windows that invite natural light. A paved driveway leads to the entrance, surrounded by lush greenery and scattered rocks.

Home in Bushkill

Charming Peaceful Retreat with Hot Tub

BrittRating, 5 stars1 month ago

We had a great 2 night stay in early spring. It was perfect for a get together for 3 couples to meet in a convenient location coming from 3 different directions. We used the hot tub and sat outside on the porch. Close to bushkill, dingmans and Milford where we went for brunch on Sunday. Cozy place.

5 out of 5 average rating, 57 reviews

A communal hot tub is framed by lush green landscaping, with a yellow umbrella providing shade nearby. Smooth stones surround the hot tub, creating a natural aesthetic, while the clear blue water reflects the sunny sky.

Condo in Vernon Township

Little Getaway at the Black Creek Sanctuary

MichelleRating, 5 stars3 weeks ago

Always a pleasure to return! My parents stayed this time and enjoyed a “staycation” They were able to relax and enjoy every moment!!!! The number one place to stay in Sussex NJ!!!!