A stone waterfall in a forested area with a stone wall in the background.

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chester vacation homes

A dock with chairs and a table by a lake, a small building on the water, and a forested hill in the background.

1. Luxury 2BR Lakefront w/ Dock & Kayaks

Luxury 2BR Lakefront w/ Dock & Kayaks
Hopatcong
9.6 out of 10, Exceptional, (15 reviews)
"Great view and stay."
United States
Byunghyun A.
The price is AED 458
AED 1,497 total
includes taxes & fees
1 Oct - 2 Oct
Luxury 2BR Lakefront w/ Dock & Kayaks
A wooden deck with a railing, leading to a building with a window and a door.

2. Secluded 6BR Retreat Near Lake Hopatcong

Secluded 6BR Retreat Near Lake Hopatcong
Roxbury Township
The price is AED 944
AED 2,322 total
includes taxes & fees
5 Oct - 6 Oct
Secluded 6BR Retreat Near Lake Hopatcong
A two-story house with a garage, stone retaining wall, and a well-maintained lawn.

3. Historic Barn View | Cozy Ground Level Retreat

Historic Barn View | Cozy Ground Level Retreat
Frelinghuysen Township
The price is AED 275
AED 438 total
includes taxes & fees
5 Oct - 6 Oct
Historic Barn View | Cozy Ground Level Retreat
A rustic outdoor setting with a fire pit, benches, and a small shed.

4. 1BR Rustic-Chic Barn Getaway with Private Fire Pit

1BR Rustic-Chic Barn Getaway with Private Fire Pit
Byram Township
8.0 out of 10, Very good, (2 reviews)
"Everything was exactly as described in the listing. It had everything we needed for our quick trip. Plenty of room for the two of us and our small dogs. There are a couple of nice grass areas to walk them around. And we found several nice trails to walk not too far away. Communication with the host was excellent and always very responsive. The check in and out process was simple. We are very satisfied and would definitely stay here again if we make it back this way someday."
United States
Ashley G.
The price is AED 302
AED 969 total
includes taxes & fees
19 Oct - 20 Oct
1BR Rustic-Chic Barn Getaway with Private Fire Pit
A dock with a Yamaha boat, a stone retaining wall, and a blue house with a balcony.

5. Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ

Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
Hopatcong
9.4 out of 10, Exceptional, (14 reviews)
"Great host and location. Easy to find and easy to park!"
United States
Daniel S.
The price is AED 735
AED 2,002 total
includes taxes & fees
6 Oct - 7 Oct
Lakeview Cozy Home - 2-Bedroom Cottage in Hopatcong, NJ
A wooden deck with a table and chairs, overlooking a lake with houses in the background.

6. Cozy Lakefront House with a private dock and lakefront.

Cozy Lakefront House with a private dock and lakefront.
Hopatcong
9.8 out of 10, Exceptional, (7 reviews)
"The home was well appointed and had a beautiful view! Steve was very responsive to all our needs."
United States
Mary Jo Y.
The price is AED 735
AED 2,587 total
includes taxes & fees
12 Oct - 13 Oct
Cozy Lakefront House with a private dock and lakefront.
A dining area with a long table, multiple chairs, a television displaying a fireplace, and a modern ceiling light fixture.

7. Lux Lakeview Experience Sleep 8

Lux Lakeview Experience Sleep 8
Hopatcong
Lux Lakeview Experience Sleep 8
A waterfront building with a sign reading 'The Windlass,' featuring a row of wooden paddle boats.

8. Lee's House - Lakeview House w/ 3 bdrm & 1 bth

Lee's House - Lakeview House w/ 3 bdrm & 1 bth
Jefferson
10.0 out of 10, Exceptional, (18 reviews)
"Amazing"
United States
Andrew
The price is AED 921
AED 1,579 total
includes taxes & fees
26 Oct - 27 Oct
Lee's House - Lakeview House w/ 3 bdrm & 1 bth
A patio area with a table and chairs, a white fence, and greenery in the background.

9. Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains

Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
Scotch Plains
9.0 out of 10, Wonderful, (9 reviews)
"Place was exactly what we needed. We were in town for a hockey camp, so we just needed somewhere to basically sleep. Our first VRBO got cancelled and I’m taking it as a blessing in disguise because this place was great!"
United States
Courtney K.
The price is AED 514
AED 1,098 total
includes taxes & fees
4 Oct - 5 Oct
Charming 2-bedroom Apartment with AC and WiFi in fabulous Scotch Plains
A hotel room with two beds, a desk, and a window with curtains.

10. 2 Queen Beds | Micfridge

2 Queen Beds | Micfridge
Piscataway
The price is AED 343
AED 393 total
includes taxes & fees
13 Oct - 14 Oct
2 Queen Beds | Micfridge
Living Room (2)

11. Historic Barn View Newton Farm House Unit

Historic Barn View Newton Farm House Unit
Frelinghuysen Township
10.0 out of 10, Exceptional, (2 reviews)
"Was easy to communicate with especially day of when we had some questions "
United States
Lauren L.
The price is AED 511
AED 710 total
includes taxes & fees
4 Oct - 5 Oct
Historic Barn View Newton Farm House Unit
A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

12. BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom

BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom
Jefferson
9.2 out of 10, Wonderful, (20 reviews)
"Very attentive hosts. Great location."
United States
Gwen V.
The price is AED 2,174
AED 3,618 total
includes taxes & fees
1 Oct - 2 Oct
BestOBothWorlds*2GWifi@HandcraftedWoodTerrace~Firepit#GameRoom
A spacious living area with a sofa, a coffee table, and a patterned rug. A staircase leads to an upper floor, and a kitchen area is visible in the background.

13. Private and Cozy 2 Bedroom House with Amenities!

Private and Cozy 2 Bedroom House with Amenities!
Union Township
8.4 out of 10, Very good, (16 reviews)
"Place was great and very neat, home setting, had everything we needed. Great place"
United States
Alicia P.
The price is AED 569
AED 943 total
includes taxes & fees
5 Oct - 6 Oct
Private and Cozy 2 Bedroom House with Amenities!
A two-story house with a balcony, a covered deck, and a dock extending into the water.

14. Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner

Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner
Jefferson
10.0 out of 10, Exceptional, (4 reviews)
"Owner Lori is a wonderful and caring host!Beautiful and charming home on the lake. Clean and comfortable accommodations with lovely views. Looking forward to a return trip!"
United States
Ann D.
The price is AED 1,378
AED 2,695 total
includes taxes & fees
3 Oct - 4 Oct
Charming Lake Home on Lake Hopatcong in a quiet cove bring a boat or Waverunner
A spacious living room with a large sectional sofa, wooden beams, large windows, and a view of the outdoors.

15. Lakefront Achieve Cabin / 3BR on 200-Acre Estate

Lakefront Achieve Cabin / 3BR on 200-Acre Estate
Blairstown
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful peaceful surrounding House has everything you need loved waking up in the morning and with two major wake up would love to come back in the summer"
United States
Christy M.
The price is AED 1,091
AED 2,386 total
includes taxes & fees
4 Oct - 5 Oct
Lakefront Achieve Cabin / 3BR on 200-Acre Estate
A lakeside setting with a fire pit and Adirondack chairs.

16. Private Cozy 2BR Lakefront, 200-Acre Estate

Private Cozy 2BR Lakefront, 200-Acre Estate
Blairstown
8.0 out of 10, Very good, (2 reviews)
"The house was very lovely. Very private, very isolated, absolute peace and quiet. Just be a little cautious when driving on the property; especially when it snowed. Perfect weekend getaway. House was spacious and pleasant. Firewood was easy to access; just a little walking but it’s not bad. Host were fast to respond with anything. The house has basic necessities such as cookware and ingredients. House can be cold when entering. Heating set up is easy. Just let it warm up a while. Directions for...
United States
Thomas S.
The price is AED 1,000
AED 2,274 total
includes taxes & fees
6 Oct - 7 Oct
Private Cozy 2BR Lakefront, 200-Acre Estate
An outdoor seating area with a sofa and chairs, surrounded by potted plants and a view of the sky.

17. Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views

Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
Glen Gardner
10.0 out of 10, Exceptional, (33 reviews)
"Great communication - beautiful property - highly recommend!"
United States
john w.
The price is AED 9,183
AED 13,716 total
includes taxes & fees
5 Oct - 6 Oct
Welcome to @ViewLaneVilla "Insta/IG" NJ Mediterranean Villa with Lake Views
A row of bar stools with a woven top table, metal legs, and a wooden counter with plants.

18. 3BD 102 Madison Ter

3BD 102 Madison Ter
Springfield
The price is AED 6,244
AED 9,137 total
includes taxes & fees
14 Oct - 15 Oct
3BD 102 Madison Ter
A spacious dining area with a long wooden table, black metal railings, and large windows offering a view of the outdoors.

19. 200-Acre Lakefront Estate / 3 Homes, Sleeps 16+

200-Acre Lakefront Estate / 3 Homes, Sleeps 16+
Blairstown
The price is AED 8,447
AED 13,698 total
includes taxes & fees
6 Oct - 7 Oct
200-Acre Lakefront Estate / 3 Homes, Sleeps 16+
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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Top Chester Hotel Reviews

Madison Hotel

Madison Hotel

8/10 Good
"The Madison Hotel is lovely, quiet, and clean. Staff were polite (aside from one slightly cranky overnight desk clerk but it was 1am, so he gets a pass). For a hotel marketed as “luxury”, it left a little to be desired (I didn’t love the bed or pillows and both seemed a bit worn), but still so much better than the typical chain hotels. The Madison has so much charm, history, and character as well as some great amenities such as a fitness center and a fantastic outdoor space and very good food on site. Super convenient to the Convent Train Station that provided an easy trip into nyc for some late night walking, dinner, and drinks without needing to worry about driving."
Nicole 2-night trip
Posted 2 hours ago
Madison Hotel

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