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Chestertown Rentals

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150 Houses

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$503

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

$237

Black Bear Cabin

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 55 minutes

Price per night from

$172

The Treehouse at Atateka Point Lodge

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$385

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 3 hours 53 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. 1 hour 51 minutes

Price per night from

$140

Beautiful coastal condo w/ Gulf views, shared pool, hot tub and beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$126

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

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$572

Gorgeous condo w/ golf court views, shared pool, and shuttle to the beach!

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 2 hours 12 minutes

Price per night from

$101

One-of-a-kind coastal condo w/Gulf views, shared pool, and easy beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$105

Adorable log home w/ a full kitchen - river frontage close by!

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$153

Dog-friendly, lakefront camp cabin w/ a dock & multiple decks

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$268

LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$345

Enormous lakefront house with high-end touches, private dock

Chestertown house

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$780

Cozy cottage with deeded lake rights - 100 steps to the beach

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$164

Family-friendly coastal condo with shared pool, hot tub and easy beach access!

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$153

Single-level, spacious house with kayaks, lake access nearby

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$190

Beautiful family friendly lakefront house with dock, beach, multiple decks

Chestertown house

5 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$555

Historic Greek Revival style home w/ screened in porch -near attractions!

Chestertown chateau

6 bedrooms / 5 bathrooms / sleeps 11

Price per night from

$847

Dog-friendly, lakefront house with 2 living areas, beach nearby

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$220

Gorgeous and spacious beachfront condo with shared pool and beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 12 minutes

Price per night from

$94

Lakefront house with private beach and dock, multiple decks

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$359

Family-friendly coastal condo with shared pool and easy beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$129

Great rentals within 20 miles that match your search

HIGHLANDS CASTLE overlooking beautiful Lake George

Bolton Landing house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 56 minutes

Price per night from

$2,820

The Gold Eagle - Cottage 2

Lake George cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$130

Lakeview Lodge steps to private association beach

Schroon Lake house

3 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 32 minutes

Price per night from

$532

The Brampton

Warrensburg house

7 bedrooms / 5 bathrooms / sleeps 17

Price per night from

$2,361

Little Moose Bungalow in the Adirondacks

Minerva bungalow

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 3 hours 38 minutes

Price per night from

$177

The Gold Eagle - Cottage 11

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$160

The Gold Eagle - Cottage 9

Lake George house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$142

Lakefront house with smaller cabin available

Lake Luzerne house

3 bedrooms / 1 bathroom / sleeps 5

“Lovely Lake House Get-a-way” If you're looking for a quiet, beautiful and simple escape, this is the perfect place! There's nothing better than enjoying a cup of coffee on the back porch with the lake right in the back yard. The peaceful surroundings and quick access to Lake George make for a great vacation for a couple or a family. My family and I had a wonderful week!

Price per night from

$225

The Gold Eagle - Cottage 15

Lake George cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$160

Poirier's Paradise

Olmstedville log cabin

2 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$562

The Gold Eagle - Cottage 4

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$130

Price per night from

$541

The Gold Eagle - Cottage 8

Lake George cottage

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$154

Together at Schroon Lake, Beach rights.

Schroon Lake farmhouse

6 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$352

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

$650

Viewing 38 of 150
rentals in Chestertown

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Top Destination reviews

Black Bear Cabin
Cozy cabin surrounded by nature

We spent a wonderful weekend at Black Bear Cabin. It was much more than what we hoped for. Wonderful getaway without neighbors. Everything was clean and nice, cabin life at it's best. Fireplace made our relaxing weekend perfect. Kitchen had all possible utilities that one could ever hope for. Beautiful plates and mugs, everything in the cabin decorated according Black Bear theme. There were six adults and two kids in our party and we fitted in nicely, even over dining table. We took a trip to Lake Placid on one day and to Hadley Mountain Hike on the other day to see amazing mountain views. There would have been many other interesting places to see nearby, but unfortunately we didn't have enough time. We can warmly recommend Black Bear Cabin!see more
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
Single-level, spacious house with kayaks, lake access nearby
Large spacious lake house

The owner could add a few things to make this a more appealing rental. Kitchen utensils were sparse and not very clean. No dishwasher, Cable TV or trash service. When on vacation you don't want to go to the landfill! The house was very clean and comfortable. The photos are a bit deceiving because you think the backyard is private and it backs up to other homes on each side of you. Not much to do in Chestertown itself and had to venture to other towns. Overall it is a very nice home that could be just a bit better if there was a little more attention to detailsee 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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