Holiday Houses in Chestertown

Updating

age 0-16
155 Results

Relevance

Price low to high

Price high to low

Reviews

155 Holiday homes

Loon Lake Retreat with Private Dock

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

19

from £187 / night

£1,213 / week

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

13

from £397 / night

£2,986 - £3,640 / week

Black Bear Cabin

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

16

Responds fast! avg. 3 hours 20 minutes

from £140 / night

£887 / week

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

3

from £186 / night

£1,120 - £1,283 / week

Green Mansions Vacation Condo

Chestertown apartment

2 bedrooms / 2 bathrooms / sleeps 6

17

Responds fast! avg. 1 hour 58 minutes

from £139 / night

£601 - £785 / week

The Treehouse at Atateka Point Lodge

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

8

from £301 / night

£2,032 - £2,485 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 45 minutes

from £85 / night

£595 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 45 minutes

from £85 / night

£595 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 45 minutes

from £85 / night

£595 / week

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

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

from £233 / night

£1,627 / week

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

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

from £247 / night

£1,725 / week

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

Chestertown house

5 bedrooms / 3 bathrooms / sleeps 6

from £469 / night

£3,279 / week

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

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 11

from £315 / night

£2,202 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 7

from £81 / night

£562 / week

NEW LISTING! Waterfront & view home w/ deck, full kitchen & WiFi!

Chestertown house

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 45 minutes

from £111 / night

£778 / week

Gorgeous and spacious beachfront condo with shared pool and beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 45 minutes

from £77 / night

£536 / week

Enormous lakefront house with high-end touches, private dock

Chestertown house

6 bedrooms / 4 bathrooms / sleeps 12

from £643 / night

£4,501 / week

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. 1 hour 45 minutes

from £85 / night

£595 / week

Gorgeous condo w/golf course and mountain views and shared pool & spa!

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 45 minutes

from £73 / night

£510 / week

Charming oceanfront cottage w/enclosed porches steps to the water! Dogs ok!

Chestertown house

5 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 45 minutes

from £183 / night

£1,281 / week

LOON LAKE luxury Ski Gore,snowmobile,canoe,kayaks

Chestertown house

3 bedrooms / 3 bathrooms / sleeps 14

3

from £280 / night

£1,862 - £1,955 / week

Lakefront house with private beach and dock, multiple decks

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

from £310 / night

£2,169 / week

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

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

from £142 / night

£994 / week

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

Chestertown chateau

6 bedrooms / 5 bathrooms / sleeps 11

from £689 / night

£4,821 / week

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

Chestertown house

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 1 hour 45 minutes

from £70 / night

£490 / week

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

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 10

1

from £120 / night

£837 / week

Great rentals within 20 miles that match your search

Gore Ski House located in the heart of North Creek

North Creek house

5 bedrooms / 2 bathrooms / sleeps 12

from £324 / night

£1,848 - £1,977 / week

Collette's Cottage 5

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

1

from £241 / night

£1,664 / week

Bolton Cabins

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 6

from £218 / night

£1,524 / week

The Gold Eagle - Cottage 14

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

from £125 / night

£684 - £864 / week

Lakemont at the Lake

Severance house

5 bedrooms / 2 bathrooms / sleeps 6

from £251 / night

£1,755 - £1,884 / week

Lake George Area, Fun Saratoga Gore Mtn, and More

Lake George house

3 bedrooms / 2 bathrooms / sleeps 6

2

from £203 / night

£1,293 - £1,616 / week

Adirondack Getaway at "Westward"

Severance house

3 bedrooms / 1 bathroom / sleeps 8

from £208 / night

£1,593 - £1,852 / week

Green Chalet at Tripp Lake

Warrensburg log cabin

4 bedrooms / 3 bathrooms / sleeps 8

1

from £273 / night

£1,801 / week

1 Bedroom Beach Unit

Lake George apartment

1 bedroom / 1 bathroom / sleeps 4

2

from £153 / night

£878 / week

Schroon River Cabin

Warrensburg log cabin

2 bedrooms / 1 bathroom / sleeps 4

4

Responds fast! avg. 3 hours 8 minutes

from £139 / night

£832 - £1,155 / week

Sunderland Cottages - Chickade, one of 7 cottages on Paradox

Paradox cottage

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 15 minutes

from £185 / night

£1,201 / week

Cozy Log House with Beautiful View

Diamond Point house

3 bedrooms / 2 bathrooms / sleeps 8

10

Responds fast! avg. 53 minutes

from £259 / night

£1,810 / week

The Gold Eagle - Cottage 12

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

from £125 / night

£684 - £864 / week

The Gold Eagle - Cottage 4

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 4

from £102 / night

£591 - £772 / week

Viewing 40 of 155
rentals in Chestertown