Chestertown Rentals

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59 Houses

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$673

Friends Lake- Quaint and New

Chestertown cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$308

The Treehouse at Atateka Point Lodge

Chestertown b&b

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$449

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 great having all the amenities for our active boys just a walk away as well as beautiful Lake George so close by! Our family has rented several times and upon each return we notice another convenience or update added to the unit. A perfect day for us includes, eating breakfast on the covered patio, followed by a hiking adventure at the many places nearby,(our kids will squeeze in some tennis or basketball too) then down the path to the lake to catch some sun, some swimming, kayaking or boating then back to the condo for a grilled dinner and campfire! Then off to the comfortable beds for a good nights sleep so we could spend the next day at beautiful Lake George! It's such a treat to enjoy all that Mother Nature has to offer and to come back to such a comfortable, cozy, and well loved condo!

Responds fast! avg. 2 hours 52 minutes

Price per night from

$168

Adirondack Cabin -steps from private lake and golf, skiing within 20 mins

Chestertown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$393

Great rentals within 20 miles that match your search

Camp Reno

Johnsburg log cabin

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 16

Responds fast! avg. 1 hour 59 minutes

Price per night from

$729

Westward, An Adirondack Getaway

Severance house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$314

Mirror Cove, Lakefront house right on Paradox Lake

Severance house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$292

Birches

Severance house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$154

Cherrybank, an Adirondack house on the lake

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$314

Fernwood, An Adirondack House at the Lake

Severance house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$314

Pinebrook, A Peaceful Adirondack Retreat

Severance house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$292

Green Chalet at Tripp Lake

Warrensburg log cabin

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$443

Lake George Getaway Rental By Million Dollar Beach

Lake George house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 11

Responds fast! avg. 49 minutes

Price per night from

$449

Poirier's Paradise

Olmstedville log cabin

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$533

Tuckaway by the lake

Severance house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$288

Ripple Bay, lakeside vacation getaway

Schroon Lake house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$320

Price per night from

$512

HIGHLANDS CASTLE overlooking beautiful Lake George

Bolton Landing house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 31 minutes

Price per night from

$9,407

'The Castle Cottage' overlooking Lake George!

Bolton Landing castle

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$1,564

'The King's Suite' in HIGHLANDS CASTLE!

Bolton Landing private room

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 2 hours 31 minutes

Price per night from

$1,227

'The Royal Bedroom' in HIGHLANDS CASTLE!

Bolton Landing private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 31 minutes

Price per night from

$1,227

The Castle Gatehouse... at Highlands Castle!

Bolton Landing house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 31 minutes

Price per night from

$1,564

The Gold Eagle - Cottage 2

Lake George cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$168

Bolton Cabins

Bolton Landing cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$265

Bolton Cottage

Bolton Landing cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$426

Lovely cottage on Lake George, NY. Dock INCLUDED

Cleverdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$225

Beautiful Lake George Adirondack Chalet

Lake George chalet

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$195

The Gold Eagle - Cottage 1

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$225

The Gold Eagle - Cottage 4

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$168

The Gold Eagle - Cottage 5

Lake George cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$196

The Gold Eagle - Cottage 3

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$168

The Gold Eagle - Cottage 6

Lake George cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$163

The Gold Eagle - Cottage 8

Lake George cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$196

The Gold Eagle - Cottage 7

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$196

The Gold Eagle - Cottage 9

Lake George house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$180

The Gold Eagle - Cottage 10

Lake George house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$180

The Gold Eagle - Cottage 11

Lake George cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$202

Viewing 38 of 59
rentals in Chestertown

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Top Destination reviews

Atateka Point Lodge and Treehouse Guest Cottage
Friends Lake at Atateka Point Lodge is a great place for family vacation.

Atateka Point Lodge was everything we hoped for in a vacation rental. The covered gazebo dock right on the lake with bench swing, table and chairs were beyond expectations. The main cottage has a full size kitchen with modern appliances. The table was large enough to seat everyone in our family and guests. There is a wood burning fireplace in the living room. The main cottage has three separate sleeping areas, a set of twin bunk beds on the porch, a double bed in the main bedroom and a set of twin beds facing the lake.There is a shower stall and toilet off the living room. The smaller updated cottage was cozy and beautifully decorated. It has a remote control gas fireplace in the living room, the kitchen in the smaller cottage is a galley style yet met our needs perfectly with half bath and washer and dryer off the living room. Upstairs there is a single bedroom with a double bed, the toilet is separate from the jetted/massage shower. The small deck off the cottage is ideal for morning coffee, reading or just enjoying the sounds of the lake. There is wifi, cable television, local telephone and we even had Verizon wireless cell phone service, however it is such a beautiful place the electronics were rarely used. Instead our days and evening were spent lakeside, fireside, grilling, playing games or in the hot tub enjoying each others company. The kayaks and canoes were used often exploring the lake. Friends Lake is so serene, and the cottage location on the lake affords you the tranquility of the lake even while other owners further up the lake used motor boats for tubing and water skiing. We live in Massachusetts but our families live about 50 minutes away, part of the reason we decided on these cottages were so they could join us. We had some family come up for the day and others after work, my brother and his wife enjoyed it so much they came two days in a row after working all day. The two cottages gave us plenty of room to enjoy not only our children but to offer siblings the opportunity to stay. Everyone was amazed at the beauty and tranquility of the lake. We were a family of four but enjoyed having both cabins so we could offer the invitation to our extended family. Between both the cottages, the covered gazebo dock and small deck there are plenty of places for everyone to have time to themselves or all together as a family. I would highly recommend Atateka Point Lodge.see more
Green Mansions Vacation Condo
Fabulous winter carnival weekend

My family and I had a wonderful stay in our green mansions condo rental. The location was perfect and the condo was beautiful. I would highly recommend this vacation rental if you are in the lake george area. We look forward to our next visit in the near future. Thank you asral family for the fabulous accomodations, it felt like home away from home.see more
The Treehouse at Atateka Point Lodge
Tree house

The most relaxed we have been in along time. The scenery & location were both beautiful. The was a lot of attention to detail & the house was very comfortable. … see more

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