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

119 Houses

Black Bear Cabin

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$150

1 / 14

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.

Responds fast! avg. 1 hour 22 minutes

Price per night from

$195

1 / 36

The Treehouse at Atateka Point Lodge

Chestertown b and b

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$225

1 / 23

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 18 minutes

Price per night from

$150

1 / 25

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$400

1 / 34

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

Responds fast! avg. 2 hours 13 minutes

Price per night from

$199

1 / 22
Viewing 38 of 119
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more