Updating...

Enter dates for more accurate prices

Chestertown Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Chestertown Rentals

134 Houses

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$456

1 / 34

Green Mansions Vacation Condo

Chestertown apartment

2 bedrooms / 2 bathrooms / sleeps 6

“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

Responds fast! avg. 2 hours 50 minutes

Price per night from

$139

1 / 25

Loon Lake Retreat with Private Dock

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

“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

Responds fast! avg. 45 minutes

Price per night from

$229

1 / 36

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 50 minutes

Price per night from

$228

1 / 22

Black Bear Cabin

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$172

1 / 15

The Treehouse at Atateka Point Lodge

Chestertown b and b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$287

1 / 23

Great rentals within 20 miles that match your search

Ripple Bay, lakeside vacation getaway

Schroon Lake house

4 bedrooms / 1 bathroom / sleeps 8

Price per night from

$297

1 / 5

Collette's Cottage 3

Lake George cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$223

1 / 7

The Gold Eagle - Cottage 10

Lake George house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$137

1 / 11

Lake George Area, Fun Saratoga Gore Mtn, and More

Lake George house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$250

1 / 14

Adirondack 1-4

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$188

1 / 6

Green Chalet at Tripp Lake

Warrensburg log cabin

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$337

1 / 20

Responds fast! avg. 3 hours 6 minutes

Price per night from

$229

1 / 6

Abanaki 1-2

Lake George cottage

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$183

1 / 7

Osage Cabin near Schroon, Gore and Lake George

Pottersville cottage

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

Price per night from

$257

1 / 9

The Gold Eagle - Cottage 4

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$126

1 / 17

GLAMP RICHARD

North River tented camp

1 bedroom / 3 bathrooms / sleeps 2

Responds fast! avg. 2 hours 1 minutes

Price per night from

$155

1 / 31

Bolton Landing Cottage-Steps to Beach!

Bolton Landing cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 41 minutes

Price per night from

$132

1 / 24

Price per night from

$522

1 / 25

Hot Tub Under the Stars

Johnsburg house

3 bedrooms / 2 bathrooms / sleeps 5

“Quiet, peaceful getaway” My family (including 2 kids under age 3) got away for a few days and had a wonderful stay. The owners had prepared a nice bonfire in the outdoor firepit and called to confirm we had arrived safely that evening. Cabin was cle

Responds fast! avg. 3 hours 4 minutes

Price per night from

$200

1 / 24

Lake front home, Paradox Lake 120 foot sandy beech

Schroon Lake house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 17 minutes

Price per night from

$490

1 / 21

The Gold Eagle - Cottage 7

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$149

1 / 14

'The King's Suite' in HIGHLANDS CASTLE!

Bolton Landing room

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 28 minutes

Price per night from

$566

1 / 31

Cozy Private Cottage on Loon Lake

Riparius cottage

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$257

1 / 29

Cherrybank, an Adirondack house on the lake

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$310

1 / 12

Lakemont at the Lake

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$310

1 / 8

Camp Reno

Johnsburg log cabin

3 bedrooms / 3 bathrooms / sleeps 16

Price per night from

$686

1 / 17

Eastward, delightful house on Paradox Lake

Severance house

4 bedrooms / 1 bathroom / sleeps 6

Price per night from

$294

1 / 5

The Gold Eagle - Cottage 9

Lake George house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$137

1 / 10

Bolton Cottage

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 8

Price per night from

$434

1 / 71

Main House 1

Diamond Point house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$206

1 / 5

The Gold Eagle - Cottage 16

Lake George cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$115

1 / 13

3 Bedroom Beach Unit

Lake George apartment

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$206

1 / 6

Responds fast! avg. 3 hours 6 minutes

Price per night from

$229

1 / 12

The Gold Eagle - Cottage 1

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 7

Price per night from

$172

1 / 17

Schroon River Cabin

Warrensburg log cabin

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 4 minutes

Price per night from

$172

1 / 20

Cozy Waterfront Home in Diamond Point on Lake George, New York

Diamond Point cottage

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$430

1 / 13

Gore Mountain ,North Creek, Lake George, Saratoga

North Creek house

6 bedrooms / 3 bathrooms / sleeps 20

Responds fast! avg. 3 hours 27 minutes

Price per night from

$573

1 / 28
Viewing 38 of 134
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more