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Search results; Over 1,000 homes in Madison

Top guest favourite

Home in Madison

Madison Bay Club House

3 bedrooms, 7 beds, 2.5 shared bathrooms

29 Aug – 3 Sept

$2,398 SGD for 5 nights

,

5.0 out of 5 average rating, 52 reviews

Guest favourite

Home in Woolford

Gorgeous Waterfront, Beach, Pool, Pets- 7 Bd /5ba

7 bedrooms, 13 beds, 5 bathrooms

29 Aug – 3 Sept

$9,730 SGD for 5 nights

4.98 out of 5 average rating, 87 reviews

Top guest favourite

Home in Woolford

Starboard on McKeil Point, w/heated pool & hot tub

6 bedrooms, 11 beds, 4.5 bathrooms

5–10 Sept

$9,148 SGD for 5 nights

4.99 out of 5 average rating, 142 reviews

Guest favourite

Home in Woolford

"Endless Summer" on the Chesapeake!

4 bedrooms, 7 beds, 2.5 bathrooms

17–22 Aug

$6,373 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Top guest favourite

Place to stay in Cambridge

Wye Three Oaks

2 bedrooms, 4 beds, 1 bathroom

7–12 Sept

$1,478 SGD for 5 nights

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Free cancellation

4.96 out of 5 average rating, 102 reviews

Home in Cambridge

Amazing Everything!

4 bedrooms, 4 beds, 4.5 bathrooms

10–15 Aug

$5,078 SGD for 5 nights

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Free cancellation

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Woolford

Waterfront Getaway with Dock

3 bedrooms, 4 beds, 2 bathrooms

23–28 Aug

$1,660 SGD for 5 nights

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Free cancellation

4.94 out of 5 average rating, 189 reviews

Home in Cambridge

Sunset on the Choptank River

4 bedrooms, 7 beds, 2.5 bathrooms

16–21 Aug

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Free cancellation

New place to stay

Top guest favourite

Farm stay in Madison

Madison Nature Getaway

1 bedroom, 2 beds, 1 bathroom

16–21 Oct

$858 SGD for 5 nights

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Free cancellation

4.98 out of 5 average rating, 227 reviews

Home in Cambridge

Family and Pet-Friendly, Waterfront with Pier

4 bedrooms, 5 beds, 1.5 bathrooms

27 Sept – 2 Oct

$2,214 SGD for 5 nights

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Free cancellation

Top guest favourite

Home in Cambridge

Relaxing Retreat on the Hudson

5 bedrooms, 5 beds, 2 bathrooms

24–29 Aug

$5,001 SGD for 5 nights

4.96 out of 5 average rating, 76 reviews

Superhost

Home in Cambridge

Drop Anchor on the Chesapeake

3 bedrooms, 5 beds, 2.5 bathrooms

17–22 Aug

$2,678 SGD for 5 nights

4.86 out of 5 average rating, 7 reviews

Home in Cambridge

280 Acre Waterfront Estate With Dock and Pool

5 bedrooms, 10 beds, 6 bathrooms

15–22 Aug

$16,562 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Holiday home in Cambridge

Very Private and Spacious Waterfront Family House

8 bedrooms, 15 beds, 6.5 bathrooms

15–22 Aug

$11,086 SGD for 7 nights

4.76 out of 5 average rating, 68 reviews

Guest favourite

Home in Cambridge

Chesapeake Bay Retreat

6 bedrooms, 14 beds, 3 bathrooms

30 Aug – 4 Sept

Extended stay discount

5.0 out of 5 average rating, 14 reviews

Top guest favourite

Home in Cambridge

Waterfront Home w/ Pool, Hot Tub, Kayaks & More

5 bedrooms, 5 beds, 4 bathrooms

22–27 Sept

$8,338 SGD for 5 nights

5.0 out of 5 average rating, 13 reviews

Superhost

Home in Woolford

The Blue Heron-Spacious Waterfront house w/ kayaks

6 bedrooms, 10 beds, 4 bathrooms

16–21 Aug

$3,391 SGD for 5 nights

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Free cancellation

4.67 out of 5 average rating, 58 reviews

Top guest favourite

Home in Cambridge

Sunset Breezes - quiet waterfront retreat

3 bedrooms, 5 beds, 2 bathrooms

23–28 Aug

$3,187 SGD for 5 nights

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Free cancellation

4.99 out of 5 average rating, 221 reviews

Guest favourite

Home in Cambridge

The Sailor’s Shanty

2 bedrooms, 3 beds, 2 bathrooms

23–28 Aug

$1,509 SGD for 5 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 13 reviews