50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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365 Vacation rentals

(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

(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 - $2200 / week

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from $200 / 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 $416 / night

$2200 / week

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from $416 / 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

(1) Excellent 

16

Chatham / West Chatham

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly

 …see more

from $175 / night

$950 / week

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from $175 / 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 $850 / night

$5950 / week

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from $850 / night

21

Chatham / South Chatham

2 6 7 nights min

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

 …see more

from $187 / night

$1300 / week

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from $187 / 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 - $2451 / week

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from $300 / 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 $750 / night

$5001 / week

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from $750 / night

(2) Excellent 

40

Cape Cod / Chatham

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning

 …see more

from $700 / night

$4901 / week

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from $700 / night

9

Chatham / North Chatham

3 6 7 nights min

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

 …see more

from $315 / night

$2200 / week

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from $315 / 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

$4100 / week

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from $586 / night

(1) Excellent 

17

Cape Cod / Chatham

4 10 7 nights min

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

 …see more

from $243 / night

$1701 / week

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from $243 / night

(1) Excellent 

27

Cape Cod / Chatham

3 6 7 nights min

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

 …see more

from $415 / night

$2901 / week

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from $415 / night

(1) Excellent 

14

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $372 / night

$2600 / week

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from $372 / night

(1) Excellent 

22

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $601 / night

$4201 / week

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from $601 / night

(1) Excellent 

18

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $843 / night

$5900 / week

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from $843 / night

20

Cape Cod / Chatham

2 4 Min stay varies

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

 …see more

from $275 / night

$1726 - $2301 / week

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from $275 / night

(1) Excellent 

17

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 $372 / night

$2600 / week

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from $372 / night

7

Chatham / North Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Private garden

 …see more

from $286 / night

$2000 / week

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from $286 / night

8

Cape Cod / Chatham

3 8 7 nights min

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

 …see more

from $415 / night

$2901 / week

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from $415 / night

18

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $415 / night

$2901 / week

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from $415 / night

25

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Suitable for children age 5+

 …see more

from $308 / night

$2150 / week

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from $308 / 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

12

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 $315 / night

$2200 - $3001 / week

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from $315 / night

(1) Excellent 

13

Cape Cod / Chatham

3 6 7 nights min

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

 …see more

from $215 / night

$1500 / week

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from $215 / night

26

Cape Cod / Chatham

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Pet friendly

 …see more

from $300 / night

$1901 - $3701 / week

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from $300 / night

22

Chatham / South Chatham

4 10 7 nights min

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

 …see more

from $415 / night

$2901 / week

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from $415 / night

(1) Excellent 

16

Cape Cod / Chatham

4 10 7 nights min

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

 …see more

from $358 / night

$2501 / week

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from $358 / night

(3) Very Good 

9

Cape Cod / Chatham

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $200 / night

$1400 / week

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from $200 / night

(2) Good 

11

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly

 …see more

from $215 / night

$1500 / week

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from $215 / night

20

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning

 …see more

from $393 / night

$2750 - $3801 / week

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from $393 / night

(4) Good 

16

Cape Cod / Chatham

2 6 7 nights min

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

 …see more

from $143 / night

$1001 - $1500 / week

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from $143 / 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

(2) Excellent 

25

Chatham / South Chatham

4 10 Min stay varies

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

 …see more

from $250 / night

$1701 - $2901 / week

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from $250 / night

11

Cape Cod / Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $250 / night

$1201 - $2351 / week

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from $250 / night

(1) Excellent 

11

Cape Cod / Chatham

3 6 7 nights min

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

 …see more

from $243 / night

$1701 / week

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from $243 / night

(1) Excellent 

17

Cape Cod / Chatham

2 6 7 nights min

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

 …see more

from $358 / night

$2501 / week

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from $358 / night

29

Cape Cod / Chatham

4 8 7 nights min

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

 …see more

from $333 / night

$2326 - $3475 / week

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from $333 / night