We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Search results; Over 1,000 homes in Pawling

Photo 1 of 6

Top guest favourite

Cottage in Pawling

Twin Lakes Designer A-frame Stone Cottage

1 bedroom, 1 bed, 1 private bathroom

27 Sept – 2 Oct

$2,768 SGD for 5 nights

,

4.99 out of 5 average rating, 184 reviews

Photo 1 of 6

Top guest favourite

Flat in Pawling

Quiet Studio Apartment in Pawling

1 bedroom, 1 king bed

9–14 Oct

$1,200 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 151 reviews

Photo 1 of 6

Top guest favourite

Home in Pawling

Historic Mansion: 6BR Retreat + Horse Sanctuary

6 bedrooms, 8 beds

19–24 Oct

$5,585 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 11 reviews

Photo 1 of 6

Home in Pawling

Quaker Hill Hideway | 7 Acres, Pool & Stargazing

3 bedrooms, 3 beds

12–17 Sept

$4,401 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews

Photo 1 of 6

Top guest favourite

Home in Pawling

Farmhouse Oasis in the Hudson Valley, Stream Views

4 bedrooms, 6 beds

1–6 Oct

$2,851 SGD for 5 nights

4.97 out of 5 average rating, 106 reviews

Photo 1 of 6

Guest favourite

Home in Pawling

Private Lake House, Retreat

2 bedrooms, 2 beds

7–12 Sept

$2,002 SGD for 5 nights

Pay $0 today

Free cancellation

4.94 out of 5 average rating, 31 reviews

Photo 1 of 6

Guest favourite

Cottage in Pawling

Forest Acres Cottage: Appalachian/Empire St Trail!

1 bedroom, 2 beds

4–9 Sept

$1,459 SGD for 5 nights

4.97 out of 5 average rating, 113 reviews

Photo 1 of 6

Top guest favourite

Home in Pawling

Country Village Getaway

2 bedrooms, 2 queen beds

1–7 Jun

$2,274 SGD for 6 nights

Free cancellation

4.93 out of 5 average rating, 40 reviews

Photo 1 of 6

Home in Holmes

Laurelwood Cottage at Sanita Hill

4 bedrooms, 5 beds

7–12 Sept

$3,130 SGD for 5 nights

Pay $0 today

Free cancellation

Photo 1 of 6

Top guest favourite

Home in Pawling

Lakefront retreat

3 bedrooms, 3 queen beds

8–13 Sept

$3,686 SGD for 5 nights

5.0 out of 5 average rating, 19 reviews

Photo 1 of 6

Top guest favourite

Flat in Holmes

Top Side

1 bedroom, 1 bed

24–29 Oct

$1,252 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 142 reviews

Photo 1 of 6

Top guest favourite

Home in Dover Plains

Somewhere That’s Green, Gameroom/Bar, Fenced yard

3 bedrooms, 4 beds

1–6 Sept

$3,059 SGD for 5 nights

5.0 out of 5 average rating, 49 reviews

Photo 1 of 6

Top guest favourite

Home in Pawling

Idyllic Lake Home-Hot tub, Woodstove-Hudson Valley

3 bedrooms, 4 beds

8–13 Sept

$3,593 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 11 reviews

Photo 1 of 6

Top guest favourite

Cabin in Holmes

Spa Cabin with 2 Suites & Hot Tub

5 bedrooms, 7 beds

1–6 Sept

$7,308 SGD for 5 nights

4.98 out of 5 average rating, 109 reviews

Photo 1 of 6

Guest favourite

Cabin in Holmes

A View From the Lakehouse

3 bedrooms, 3 beds

1–6 Sept

$4,226 SGD for 5 nights

4.95 out of 5 average rating, 55 reviews

Photo 1 of 6

Top guest favourite

Home in Pawling

Quaker Hill Cottage

2 bedrooms, 2 beds

8–13 Sept

5.0 out of 5 average rating, 14 reviews

Photo 1 of 6

Guest favourite

Home in Mahopac

Peaceful & Spacious Retreat

5 bedrooms, 5 beds

7–12 Sept

$3,756 SGD for 5 nights

4.96 out of 5 average rating, 176 reviews

Photo 1 of 6

Guest favourite

Cottage in Dover Plains

Charming Country House

4 bedrooms, 4 queen beds

1–6 Sept

$2,521 SGD for 5 nights

5.0 out of 5 average rating, 25 reviews

Photo 1 of 6

Top guest favourite

Home in New Fairfield

Best Candlewood Direct Lakefront Location

5 bedrooms, 7 beds

16–21 Sept

$5,547 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews