Chestertown Rentals

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132 Houses

(18) Excellent 

36

Loon Lake Retreat with Private Dock

New York / Chestertown

Chestertown house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
“Great area and very nice house” My family and I had a great 4 day stay at this Loon Lake house. Comfortable beds, roomy living room, dining area and kitchen, fireplace ( with lots of cut wood to burn), TV, internet, etc. Felt right at home. The owners
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Price per night from

$230

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$230

(13) Excellent 

34

Atateka Point Lodge and Treehouse Guest Cottage

New York / Chestertown

Chestertown cottage

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 26 mi
  • Child Friendly

Price per night from

$458

Price per night from

$458

(2) Very Good 

22

Friends Lake- Quaint and New

New York / Chestertown

Chestertown cottage

2 7 2 nights min

  • 2 bedrooms
  • sleeps 7
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 mi
  • Child Friendly

Price per night from

$228

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$228

(17) Excellent 

Certificate of Excellence

25

Green Mansions Vacation Condo

New York / Chestertown

Chestertown apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Ski
“Surrounded by Nature with the comforts of home.” With a peaceful, private lake just a footpath away from this completely updated unit, you can't go wrong! Despite all the modern touches the unit holds, it has such a cozy "cabin" feel to it. It was g
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Certificate of Excellence

Price per night from

$139

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$139

(13) Excellent 

12

Black Bear Cabin

New York / Chestertown

Chestertown log cabin

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Private garden

Price per night from

$172

Price per night from

$172

(6) Excellent 

23

The Treehouse at Atateka Point Lodge

New York / Chestertown

Chestertown b and b

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$315

Price per night from

$315

Great rentals within 20 miles that match your search

Distance approx 16.11 km from Chestertown

5

Ripple Bay, lakeside vacation getaway

New York / Schroon Lake

Schroon Lake house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$299

Price per night from

$299

Distance approx 9.71 km from Chestertown Show on Map

15

Gore Ski House located in the heart of North Creek

New York / North Creek

North Creek house

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Suitable for children age 5+
  • Ask about pets

Price per night from

$401

Price per night from

$401

Distance approx 12.48 km from Chestertown

(9) Excellent 

34

The Adirondack Getaway

New York / Minerva

Minerva house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Child Friendly

Price per night from

$173

Responds fast!
avg. 1 hour 6 minutes

Price per night from

$173

Distance approx 16.17 km from Chestertown

(1) Excellent 

12

Cherrybank, an Adirondack house on the lake

New York / Severance

Severance house

5 6 7 nights min

  • 5 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$312

Price per night from

$312

Distance approx 16.06 km from Chestertown

11

Breezes, a four season house by the lake

New York / Severance

Severance house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Child Friendly

Price per night from

$276

Price per night from

$276

Distance approx 14.96 km from Chestertown

(3) Very Good 

31

Authentic Adirondack Bird Camp

New York / North River

North River log cabin

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 5 mi
  • Ski
  • Child Friendly

Price per night from

$201

Responds fast!
avg. 3 hours 10 minutes

Price per night from

$201

Distance approx 12.08 km from Chestertown

(1) Excellent 

11

Baker Brook Lodge

New York / Bakers Mills

Bakers Mills lodge

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Child Friendly
  • Ask about pets

Price per night from

$173

Price per night from

$173

Distance approx 8.47 km from Chestertown

(1) Excellent 

6

Mohawk

New York / Lake George

Lake George house

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$196

Price per night from

$196

Distance approx 16.13 km from Chestertown

(3) Very Good 

10

Peaceful Adirondack house by the Lake

New York / Severance

Severance house

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Pet Friendly

Price per night from

$292

Price per night from

$292

Distance approx 17.06 km from Chestertown

(2) Excellent 

17

Lake George Getaway Rental By Million Dollar Beach

New York / Lake George

Lake George house

4 11 7 nights min

  • 4 bedrooms
  • sleeps 11
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$444

Price per night from

$444

Distance approx 15.65 km from Chestertown

24

Cozy Garnet Hill Home by Hiking & Gore Mtn Skiing!

New York / North River

North River house

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$229

Responds fast!
avg. 9 minutes

Price per night from

$229

Distance approx 16.81 km from Chestertown

(4) Very Good 

7

Collette's Cottage 3

New York / Lake George

Lake George cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$224

Price per night from

$224

Distance approx 18.11 km from Chestertown

8

Sunderland Cottages - Chickadee

New York / Paradox

Paradox cottage

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Child Friendly

Price per night from

$197

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$197

Distance approx 16.53 km from Chestertown

10

Pine Grove Cottages #9/10 - charming Adirondack cabin in Lake George Village

New York / Lake George

Lake George cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$284

Price per night from

$284

Distance approx 8.47 km from Chestertown

(2) Average 

8

Tamarack

New York / Lake George

Lake George cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$213

Price per night from

$213

Distance approx 6.56 km from Chestertown Show on Map

(1) Excellent 

27

The Brampton

New York / Warrensburg

Warrensburg house

7 17 2 nights min

  • 7 bedrooms
  • sleeps 17
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$2,297

Price per night from

$2,297

Distance approx 9.05 km from Chestertown

(2) Very Good 

16

Beautiful Log House In Bolton In Lake George

New York / Bolton Landing

Bolton Landing house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$288

Price per night from

$288

Distance approx 8.47 km from Chestertown

(1) Very Good 

5

Main House 1

Lake George / Diamond Point

Diamond Point house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Pet Friendly

Price per night from

$219

Price per night from

$219

Distance approx 8.47 km from Chestertown

(2)  

6

3 Bedroom Beach Unit

New York / Lake George

Lake George apartment

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$219

Price per night from

$219

Distance approx 16.81 km from Chestertown

(1) Very Good 

6

Collette's Cottage 2

New York / Lake George

Lake George cottage

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$288

Price per night from

$288

Distance approx 8.47 km from Chestertown

(1)  

7

Abanaki 1-2

New York / Lake George

Lake George cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$196

Price per night from

$196

Distance approx 8.47 km from Chestertown

(1) Very Good 

5

Main House 1 & 2

New York / Lake George

Lake George house

6 16 2 nights min

  • 6 bedrooms
  • sleeps 16
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$425

Price per night from

$425

Distance approx 8.47 km from Chestertown

(2) Very Good 

6

1 Bedroom Beach Unit

New York / Lake George

Lake George apartment

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$190

Price per night from

$190

Distance approx 15.37 km from Chestertown

17

The Gold Eagle - Cottage 1

New York / Lake George

Lake George cottage

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$173

Price per night from

$173

Distance approx 15.37 km from Chestertown

12

The Gold Eagle - Cottage 12

New York / Lake George

Lake George cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$155

Price per night from

$155

Distance approx 15.37 km from Chestertown

19

The Gold Eagle - Cottage 6

New York / Lake George

Lake George cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$127

Price per night from

$127

Distance approx 15.37 km from Chestertown

18

The Gold Eagle - Cottage 14

New York / Lake George

Lake George cottage

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$155

Price per night from

$155

Distance approx 15.37 km from Chestertown

13

The Gold Eagle - Cottage 16

New York / Lake George

Lake George cottage

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$115

Price per night from

$115

Distance approx 9.88 km from Chestertown

71

Bolton Cottage

New York / Bolton Landing

Bolton Landing cottage

2 8 min stay varies

  • 2 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$437

Price per night from

$437

Distance approx 18.17 km from Chestertown

12

Sunderland Cottages - Whippoorwill

New York / Paradox

Paradox cottage

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly

Price per night from

$173

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$173

Distance approx 11.73 km from Chestertown

(18) Excellent 

31

NICE, BIG, FRIENDLY HOUSE ON LAKE GEORGE. June weeks for $2,950; $3,950.

Lake George / Diamond Point

Diamond Point house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$201

Price per night from

$201

Distance approx 9.67 km from Chestertown

5

The Castle Gatehouse... at Highlands Castle!

New York / Bolton Landing

Bolton Landing house

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 0.5 mi
  • Air conditioning

Price per night from

$684

Responds fast!
avg. 2 hours 28 minutes

Price per night from

$684