50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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312 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 $278 / night

$1614 - $4532 / week

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from $278 / 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

(1) Excellent 

27

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $851 / night

$5950 / week

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from $851 / night

8

Chatham / North Chatham

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $286 / night

$2000 - $3001 / week

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from $286 / 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

11

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children

 …see more

from $643 / night

$4500 / week

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from $643 / night

(3) Very Good 

9

Cape Cod / Chatham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

 …see more

from $251 / night

$1500 / week

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from $251 / 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

(16) Excellent 

46

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

21

Cape Cod / Chatham

1 2 3 nights min

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

 …see more

from $303 / night

$2118 - $2470 / week

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from $303 / night

13

Chatham / North Chatham

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $501 / night

$3501 - $7451 / week

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from $501 / night

(1) Excellent 

23

Cape Cod / Chatham

4 10 7 nights min

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

 …see more

from $586 / night

$4101 / week

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from $586 / night

17

Chatham / North Chatham

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $643 / night

$4500 - $4950 / week

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from $643 / night

11

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

17

Cape Cod / Chatham

3 7 7 nights min

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

 …see more

from $401 / night

$2801 / week

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from $401 / night

34

Chatham / North Chatham

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

from $751 / night

$5000 / week

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from $751 / night

(4) Excellent 

12

Cape Cod / Chatham

2 5 7 nights min

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

 …see more

from $222 / night

$1550 / week

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from $222 / night

14

Chatham / North Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $401 / night

$2801 - $3001 / week

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from $401 / night

11

Chatham / South Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $401 / night

$2801 / week

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from $401 / night

22

Cape Cod / Chatham

4 11 7 nights min

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

 …see more

from $529 / night

$3701 / week

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from $529 / night

23

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

11

Chatham / South Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $200 / night

$1400 - $2100 / 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

(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

(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 $303 / night

$1513 - $2521 / week

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from $303 / night

11

Chatham / North Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from $286 / night

$2000 - $2600 / week

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from $286 / night

12

Chatham / West Chatham

2 5 7 nights min

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

 …see more

from $200 / night

$1400 / week

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from $200 / night

(1) Excellent 

41

Cape Cod / Chatham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly

 …see more

from $601 / night

$4000 - $5200 / week

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from $601 / night

(1) Excellent 

21

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $486 / night

$3400 / week

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from $486 / night

20

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $429 / night

$3001 - $6200 / week

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from $429 / night

19

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $343 / night

$2401 / week

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from $343 / night

(1) Excellent 

17

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $429 / night

$3001 / week

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from $429 / night

12

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

(1) Very Good 

12

Cape Cod / Chatham

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $329 / night

$2301 / week

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from $329 / night

16

Cape Cod / Chatham

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $272 / night

$1900 - $2401 / week

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from $272 / night

(1) Excellent 

18

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $429 / night

$3001 / week

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from $429 / night

17

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $358 / night

$2500 / week

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from $358 / night

19

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $1029 / night

$7201 / week

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from $1029 / night

8

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

21

Cape Cod / Chatham

3 7 7 nights min

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

 …see more

from $233 / night

$1626 - $2551 / week

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from $233 / night