50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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372 Vacation rentals

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(3) Excellent 

44

Vacation home in South Chatham

Chatham / South Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 0.6 mi
  • Child friendly
  • Air conditioning
Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6-8 comfortably. Up to 10 including a pullout sleeper sofa. All rooms are brig  …see more

from $275 / night

$1601 - $4495 / week

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from $275 / night

39

Vacation home with golf nearby in West Chatham

Chatham / West Chatham

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Suitable for children age 5+
ACCOMMODATIONS: 3 bedrooms plus den with 2.5 baths. Accommodating 8-10 people. Master suite: king bed w/en suite Guest room 1: queen bed Guest room 2: four twin beds (2 bunks) Guest room 3: den w/full bed Living room Dining room seats 8 (addition kitchen table sea  …see more

from $415 / night

$2201 / week

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from $415 / night

36

Chatham / North Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $501 / night

$3501 - $5501 / week

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from $501 / night

(16) Excellent 

47

Cape Cod / Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Child friendly

 …see more

from $275 / night

$1601 - $4495 / week

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from $275 / night

0

Chatham / South Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $86 / night

$601 - $1500 / week

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from $86 / night

24

Chatham / North Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $175 / night

$1449 - $3400 / week

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from $175 / night

0

Chatham / South Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $401 / night

$2801 / week

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from $401 / night

0

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $200 / night

$1400 / week

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from $200 / night

12

Chatham / South Chatham

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $136 / night

$950 - $1201 / week

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from $136 / night

(4) Excellent 

19

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly

 …see more

from $200 / night

$1400 - $2201 / week

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from $200 / night

(1) Excellent 

23

Chatham / West Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Child friendly

 …see more

from $476 / night

$3001 / week

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from $476 / night

0

Chatham / South Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $200 / night

$1400 - $2100 / week

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from $200 / night

0

Chatham / North Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $286 / night

$2000 - $2600 / week

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from $286 / night

0

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $143 / night

$1001 / week

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from $143 / night

0

Chatham / South Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $429 / night

$3001 / week

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from $429 / night

0

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $215 / night

$1500 / week

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from $215 / night

0

Chatham / North Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $143 / night

$1001 - $1601 / week

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from $143 / night

0

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $193 / night

$1351 - $2051 / week

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from $193 / night

38

Chatham / West Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $198 / night

$1376 - $2600 / week

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from $198 / night

12

Chatham / West Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $172 / night

$1201 - $1601 / week

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from $172 / night

17

Chatham / West Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $251 / night

$1750 / week

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from $251 / night

10

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children

 …see more

from $336 / night

$2350 / week

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from $336 / night

13

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning

 …see more

from $151 / night

$1050 - $1400 / week

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from $151 / night

47

Cape Cod / Chatham

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Ask about children

 …see more

from $415 / night

$2201 / week

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from $415 / night

20

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets

 …see more

from $286 / night

$2000 - $3001 / week

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from $286 / night

(2) Excellent 

14

Chatham / West Chatham

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $300 / night

$1500 - $2500 / week

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from $300 / night

0

Cape Cod / Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $326 / night

$2275 / week

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from $326 / night

41

Cape Cod / Chatham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly

 …see more

from $300 / night

$1500 - $2401 / week

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from $300 / night

0

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $151 / night

$1050 - $1500 / week

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from $151 / night

10

Cape Cod / Chatham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $260 / night

$1900 - $2500 / week

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from $260 / night

(1) Excellent 

27

Cape Cod / Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $273 / night

$1900 - $3800 / week

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from $273 / night

0

Cape Cod / Chatham

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $186 / night

$1300 - $2000 / week

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from $186 / night

0

Chatham / South Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $215 / night

$1500 - $2401 / week

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from $215 / night

14

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $486 / night

$3400 / week

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from $486 / night

0

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets

 …see more

from $129 / night

$900 - $1626 / week

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from $129 / night

21

Cape Cod / Chatham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning

 …see more

from $300 / night

$2100 - $2450 / week

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from $300 / night

0

Cape Cod / Chatham

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $715 / night

$5000 - $6500 / week

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from $715 / night

0

Cape Cod / Chatham

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Ask about pets

 …see more

from $158 / night

$1101 / week

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from $158 / night

0

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $86 / night

$601 - $1801 / week

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from $86 / night

0

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $329 / night

$2301 / week

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from $329 / night