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Chestertown Rentals

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69 Houses

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$543

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 are very nice and I talked to them several times on the phone prior to the visit and they made me feel welcome. The area is great, the lake is beautiful and the trails/woods are cool to explore. My wife and son were sad to leave and actually missed the house when we got home. We all had a blast and will definitely be back again for an even longer stay.

Price per night from

$247

The Treehouse at Atateka Point Lodge

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$396

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 42 minutes

Price per night from

$228

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. 3 hours 12 minutes

Price per night from

$172

NEW LISTING! Lakefront cabin with sandy beach, dock, multiple fireplaces

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 3 hours 37 minutes

Price per night from

$500

Lakefront house with private beach and dock, multiple decks

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 37 minutes

Price per night from

$422

Great rentals within 20 miles that match your search

Poirier's Paradise

Olmstedville log cabin

2 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$615

Bolton Cabins

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$306

Dock in Katskill Bay and swimming in Sandy Bay _Newly Renovated Home

Cleverdale house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$595

Lovely cottage on Lake George, NY. Dock INCLUDED

Cleverdale cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$259

Beautiful Lake George Adirondack Chalet

Lake George chalet

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$154

NICE, BIG, FRIENDLY HOUSE ON LAKE GEORGE.

Diamond Point house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$266

Price per night from

$552

HIGHLANDS CASTLE overlooking beautiful Lake George

Bolton Landing house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 33 minutes

Price per night from

$7,030

Dog-friendly, lakefront house w/ a dock, sandy beach, & screened porch

Pottersville house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$231

The Castle Gatehouse... at Highlands Castle!

Bolton Landing house

3 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 33 minutes

Price per night from

$1,363

Go Rustic! The Annex at Catamount Loj

Pottersville cottage

4 bedrooms / 1 bathroom / sleeps 4

Price per night from

$160

Great lakeside condo w/ lake views, gas fireplace, jetted tub, cable, WiFi

Bolton Landing townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 37 minutes

Price per night from

$290

'The Castle Cottage' overlooking Lake George!

Bolton Landing castle

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 33 minutes

Price per night from

$1,326

'The Royal Bedroom' in HIGHLANDS CASTLE!

Bolton Landing private room

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 33 minutes

Price per night from

$1,105

'The King's Suite' in HIGHLANDS CASTLE!

Bolton Landing private room

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 33 minutes

Price per night from

$1,101

Lake George 4-Bedroom Waterfront Home

Bolton Landing house

4 bedrooms / 3 bathrooms / sleeps 8

“Best family vacation spot ever!” Our week at Vista View was the best vacation that our family has had in many years. The home is very comfortable, well appointed and perfectly situated in proximity to Lake George, and to the town of Bolton Landing. Cheryl and Buzz gave great attention to detail in everything from the décor of the home to the comfort of the beds. Abundant towels and kitchen appliances made the week feel like "home". Buzz and Cheryl were very hospitable hosts as well. They offered great tips on what to see around the lake. Our grand children loved the sheltered and private beach area, including the very clear water. We have wonderful memories of our stay at "Vista View", and intend to make it our family's lodging spot on Lake George as often as we can.

Price per night from

$633

Pinebrook, A Peaceful Adirondack Retreat

Severance house

5 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$299

Camp Reno

Johnsburg log cabin

3 bedrooms / 3 bathrooms / sleeps 16

Responds fast! avg. 3 hours 41 minutes

Price per night from

$748

Camp Little Notch

Fort Ann tented camp

8 bedrooms / 8 bathrooms / sleeps 4

Price per night from

$57

Fernwood, An Adirondack House at the Lake

Severance house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$315

Lakeview Lodge steps to private association beach

Schroon Lake house

3 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 18 minutes

Price per night from

$508

Lake George Getaway Rental By Million Dollar Beach

Lake George house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 43 minutes

Price per night from

$455

Eastward, delightful house on Paradox Lake

Severance house

4 bedrooms / 1 bathroom / sleeps 6

Price per night from

$296

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

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$327

Tuckaway by the lake

Severance house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$282

Mirror Cove, Lakefront house right on Paradox Lake

Severance house

4 bedrooms / 1 bathroom / sleeps 6

Price per night from

$295

Cherrybank, an Adirondack house on the lake

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$317

Lakemont at the Lake

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$320

Westward, An Adirondack Getaway

Severance house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$310

Breezes, a four season house by the lake

Severance house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$337

Baker Brook Lodge

Bakers Mills lodge

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$172

Viewing 38 of 69
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
Loon Lake Retreat with Private Dock
Lovely place to stay at Loon Lake

We (my family, 5 adults) stayed here for 2 nights and we all agreed that it was a lovely place. The house is in top condition with an extremely well equipped kitchen (everything you could need was there). The house is very tastefully decorated and has a nice cosy feel to it. We used the outdoor grill and it worked perfectly. I liked that very thorough instructions and guidance was given on an information sheet in the kitchen as well. The wifi worked well too. Loon Lake itself is across the road and down a little path. We really enjoyed out stay here. … 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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