Search 105,200+ Vacation Rentals

Chatham Vacation Rentals & Apartments with Swimming Pool - 46 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

46 Vacation rentals

Filters applied: Swimming pool

1 / 52

Chatham House

  • 8
  • 16
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$5,428.00

Inquire

from $5,428.00 / night

1 / 46

Chatham House

  • 6
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,786.00

Inquire

from $1,786.00 / night

1 / 43

Chatham House

  • 4
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$1,428.00

Inquire

from $1,428.00 / night

(1)

1 / 30

Chatham House

  • 4
  • 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$928.00

Excellent (1 reviews)

Inquire

from $928.00 / night

1 / 39

Chatham House

  • 5
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly

$976.00

Inquire

from $976.00 / night

1 / 42

Chatham House

  • 5
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly

$1,438.00

Inquire

from $1,438.00 / night

1 / 35

Chatham House

  • 5
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$928.00

Inquire

from $928.00 / night

Your search has been expanded 19.3 miles to include more rentals

(4)

1 / 54

Barnstable House - 17.3 miles away

  • 5
  • 10
  • 7 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Ask about children

$786.00

Excellent (4 reviews)

Inquire

from $786.00 / night

1 / 47

Orleans House - 4.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$1,233.00

Inquire

from $1,233.00 / night

(5)

1 / 12

Dennis Port House - 9.6 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$85.00

Excellent (5 reviews)

Inquire

from $85.00 / night

1 / 29

West Harwich House - 7.7 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$514.00

Inquire

from $514.00 / night

1 / 31

Orleans House - 6.9 miles away

  • 5
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly

$1,357.00

Inquire

from $1,357.00 / night

1 / 35

East Orleans House - 7 miles away

  • 6
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly

$653.00

Inquire

from $653.00 / night

1 / 40

Brewster House - 7.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$440.00

Inquire

from $440.00 / night

1 / 48

Orleans House - 7.3 miles away

  • 10
  • 24
  • min stay varies
  • Swimming pool
  • Child friendly

$1,952.00

Inquire

from $1,952.00 / night

1 / 49

Orleans House - 8.3 miles away

  • 4
  • 15
  • min stay varies
  • Swimming pool
  • Child friendly

$1,541.00

Inquire

from $1,541.00 / night

1 / 31

Hyannis Port House - 18 miles away

  • 6
  • 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$2,142.00

Inquire

from $2,142.00 / night

1 / 29

Brewster House - 7.8 miles away

  • 3
  • 7
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$308.00

Inquire

from $308.00 / night

1 / 51

Orleans House - 8.2 miles away

  • 5
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$514.00

Inquire

from $514.00 / night

(1)

1 / 34

Orleans House - 7.1 miles away

  • 5
  • 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$771.00

Excellent (1 reviews)

Inquire

from $771.00 / night

(1)

1 / 26

Yarmouth Port House - 13.1 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly

$697.00

Excellent (1 reviews)

Inquire

from $697.00 / night

1 / 18

Yarmouth House - 13.3 miles away

  • 3
  • 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

$285.00

Inquire

from $285.00 / night

(4)

1 / 17

Dennis Port House - 9.1 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly

$213.00

Very Good (4 reviews)

Inquire

from $213.00 / night

1 / 37

West Hyannisport Apartment - 19.3 miles away

  • 3
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$501.00

Inquire

from $501.00 / night

1 / 11

Brewster House - 7.8 miles away

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$462.00

Inquire

from $462.00 / night

1 / 27

Dennis Port House - 9.9 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$215.00

Inquire

from $215.00 / night

1 / 27

Brewster House - 5.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$462.00

Inquire

from $462.00 / night

1 / 14

Dennis Port House - 9.1 miles away

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly

$79.00

Inquire

from $79.00 / night

1 / 20

Brewster House - 7.8 miles away

  • 3
  • 9
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$360.00

Inquire

from $360.00 / night

1 / 39

Brewster House - 5.5 miles away

  • 7
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

$719.00

Inquire

from $719.00 / night

1 / 13

South Dennis House - 10.1 miles away

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$251.00

Inquire

from $251.00 / night

1 / 30

South Dennis House - 9.9 miles away

  • 3
  • 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$251.00

Inquire

from $251.00 / night

1 / 26

Dennis Port Condo - 9.9 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$251.00

Inquire

from $251.00 / night

1 / 34

West Harwich House - 7.4 miles away

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Child friendly

$2,001.00

Inquire

from $2,001.00 / night

1 / 27

Orleans House - 7.7 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$31.00

Book

from $31.00 / night

1 / 16

Dennis Port Studio - 9.6 miles away

  • -1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$72.00

Inquire

from $72.00 / night

1 / 26

Wellfleet House - 18 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$31.00

Book

from $31.00 / night

1 / 26

Harwich House - 3.9 miles away

  • 8
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$572.00

Inquire

from $572.00 / night

(8)

1 / 34

Dennis Port House - 8.4 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$429.00

Excellent (8 reviews)

Inquire

from $429.00 / night

1 / 19

West Harwich House - 8 miles away

  • 6
  • 20
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$501.00

Inquire

from $501.00 / night