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Holiday Houses in Chestertown

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103 Holiday homes

Loon Lake Retreat with Private Dock

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 8

20

from £180 / night

£1,255 - £1,339 / week

Atateka Point Lodge and Treehouse Guest Cottage

Chestertown cottage

4 bedrooms / 3 bathrooms / sleeps 10

15

from £354 / night

£2,479 - £3,630 / week

Black Bear Cabin

Chestertown log cabin

2 bedrooms / 2 bathrooms / sleeps 4

19

Responds fast! avg. 1 hour 31 minutes

Travellers’ Choice award

from £126 / night

£797 / week

Friends Lake- Quaint and New

Chestertown cottage

2 bedrooms / 2 bathrooms / sleeps 7

3

Responds fast! avg. 2 hours 45 minutes

from £167 / night

£1,087 - £1,234 / week

Green Mansions Vacation Condo

Chestertown apartment

2 bedrooms / 2 bathrooms / sleeps 6

18

Responds fast! avg. 3 hours 30 minutes

from £126 / night

£669 / week

The Treehouse at Atateka Point Lodge

Chestertown b&b

2 bedrooms / 2 bathrooms / sleeps 4

9

from £296 / night

£2,026 - £2,617 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 56 minutes

from £172 / night

£1,201 / 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. 2 hours 56 minutes

from £171 / night

£1,193 / week

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

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 47 minutes

from £230 / night

£1,610 / week

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

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from £239 / night

£1,672 / week

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

Chestertown house

5 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 47 minutes

from £391 / night

£2,734 / week

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

from £364 / night

£2,547 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 47 minutes

from £111 / night

£773 / week

Waterfront & family-friendly home w/ deck,great views, full kitchen & WiFi!

Chestertown house

1 bedroom / 1 bathroom / sleeps 6

Responds fast! avg. 2 hours 56 minutes

from £185 / night

£1,294 / week

Gorgeous and spacious beachfront condo with shared pool and beach access

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 45 minutes

from £153 / night

£1,066 / week

Enormous lakefront house with high-end touches, private dock

Chestertown house

6 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 47 minutes

from £562 / night

£3,929 / 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. 2 hours 56 minutes

from £185 / night

£1,294 / week

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

Chestertown house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 56 minutes

from £117 / night

£814 / week

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

Chestertown house

5 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 56 minutes

from £179 / night

£1,247 / week

Lakefront house with private beach and dock, multiple decks

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 9

Responds fast! avg. 3 hours 37 minutes

from £307 / night

£2,145 / week

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

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from £157 / night

£1,095 / week

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

Chestertown chateau

6 bedrooms / 5 bathrooms / sleeps 11

Responds fast! avg. 2 hours 47 minutes

from £617 / night

£4,315 / 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. 2 hours 56 minutes

from £120 / night

£838 / week

Single-level, spacious house w/ firepit & spacious yard - lake access nearby

Chestertown house

4 bedrooms / 2 bathrooms / sleeps 6

1

Responds fast! avg. 2 hours 47 minutes

from £132 / night

£920 / week

Gorgeous, lakefront home w/ a firepit, two living areas, & a sunroom

Chestertown house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 2 hours 47 minutes

from £264 / night

£1,847 / week

Private family-friendly home w/ game room, high-speed WiFi, & wraparound deck

Chestertown house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 47 minutes

from £169 / night

£1,183 / week

Great rentals within 20 miles that match your search

Poirier's Paradise

Olmstedville log cabin

2 bedrooms / 3 bathrooms / sleeps 10

from £447 / night

£2,354 / week

Bolton Cabins

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 6

from £222 / night

£1,553 / week

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

Cleverdale house

3 bedrooms / 2 bathrooms / sleeps 8

from £433 / night

£3,031 / week

Lovely cottage on Lake George, NY. Dock INCLUDED

Cleverdale cottage

1 bedroom / 1 bathroom / sleeps 3

from £189 / night

£1,318 / week

Beautiful Lake George Adirondack Chalet

Lake George chalet

3 bedrooms / 2 bathrooms / sleeps 8

1

from £112 / night

£784 - £1,180 / week

Bolton Cottage

Bolton Landing cottage

2 bedrooms / 1 bathroom / sleeps 8

from £345 / night

£2,414 / week

Lake George Getaway Rental By Million Dollar Beach

Lake George house

4 bedrooms / 4 bathrooms / sleeps 11

3

Responds fast! avg. 3 hours 23 minutes

from £367 / night

£2,569 / week

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

Lake George cottage

2 bedrooms / 1 bathroom / sleeps 6

from £233 / night

£1,125 / week

from £402 / night

£2,811 / week

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

Pottersville house

3 bedrooms / 1 bathroom / sleeps 6

from £168 / night

£1,175 / week

Adirondacks Year Round Chalet

Minerva chalet

4 bedrooms / 3 bathrooms / sleeps 8

1

from £216 / night

£1,117 - £2,323 / week

Go Rustic! The Annex at Catamount Loj

Pottersville cottage

4 bedrooms / 1 bathroom / sleeps 4

16

from £116 / night

£710 / week

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

from £211 / night

£1,474 / week

Lakeview Lodge steps to private association beach

Schroon Lake house

3 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 1 hour 14 minutes

from £386 / night

£2,568 / week

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rentals in Chestertown