Chestertown Rentals

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New York
Chestertown

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Air conditioning (1)
Wireless Internet (4)
Washing machine (6)
Jacuzzi or hot tub (2)

Garden (1)
Internet access (6)
DVD player (4)
Grill (5)
Fireplace (4)
Dishwasher (5)

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Pets allowed (1)
Children under 5 (6)
Parking (6)
Non-Smoking property (6)

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Beach or lakeside relaxation (5)
Skiing – property near ski resort (1)
Walking trips (3)
Tennis in town (1)

Water sports (3)
Horse riding (5)
Fishing (5)
Cycling trips (2)
Golf course on site or within 15 min walk (1)
Lakefront (5)
Golf within 30mins drive (3)
Mountain Views (3)
Waterfront (2)

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132 Houses

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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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Map

Price per night from

$230

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$230

Details

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

Map

Price per night from

$458

Price per night from

$458

Details

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

Map

Price per night from

$228

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$228

Details

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

Map

Price per night from

$139

Responds fast!
avg. 2 hours 3 minutes

Price per night from

$139

Details

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

Map

Price per night from

$172

Price per night from

$172

Details

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

Map

Price per night from

$315

Price per night from

$315

Details

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

Map

Price per night from

$401

Price per night from

$401

Details

Distance approx 12.48 km from Chestertown

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

Details

Distance approx 16.17 km from Chestertown

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

Details

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

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

Details

Distance approx 12.08 km from Chestertown

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

Details

Distance approx 8.47 km from Chestertown

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

Details

Distance approx 16.13 km from Chestertown

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

Details

Distance approx 17.06 km from Chestertown

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

Details

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

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

Details

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

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

Details

Distance approx 6.56 km from Chestertown Show on Map

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

Map

Price per night from

$2,297

Price per night from

$2,297

Distance approx 9.05 km from Chestertown

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

Details

Distance approx 8.47 km from Chestertown

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

Details

Distance approx 8.47 km from Chestertown

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

Details

Distance approx 16.81 km from Chestertown

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

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

Details

Distance approx 8.47 km from Chestertown

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

Details

Distance approx 8.47 km from Chestertown

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

Details

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

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

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