Vacation Rentals & Houses in Chatham

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2,180 houses

24

Chatham Cape Cod Vacation Rental (13059)

Cape Cod / Chatham

Chatham house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$573

Price per night from

$573

(6) Excellent 

20

Beautiful sunsets in Chatham!

Cape Cod / Chatham

Chatham house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.48 mi
  • Child Friendly

Price per night from

$458

Price per night from

$458

14

7442 Bevan

Cape Cod / Chatham

Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$242

Price per night from

$242

(1) Excellent 

41

Quintessential Cape Cod Vacation Home in N.Chatham

Cape Cod / Chatham

Chatham house

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.4 mi
  • Child Friendly

Price per night from

$782

Price per night from

$782

14

Chatham Cape Cod Vacation Rental (4983)

Cape Cod / Chatham

Chatham house

2 4 7 nights min

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

Price per night from

$229

Price per night from

$229

15

8325 Kane, Catherine

Cape Cod / Chatham

Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$171

Price per night from

$171

(1) Excellent 

21

South Chatham Cape Cod Vacation Rental (2400)

Cape Cod / Chatham

Chatham house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$345

Price per night from

$345

14

Chatham Cape Cod Vacation Rental (8560)

Cape Cod / Chatham

Chatham house

3 6 7 nights min

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

Price per night from

$221

Price per night from

$221

20

Chatham Cape Cod Vacation Rental (8233)

Cape Cod / Chatham

Chatham house

2 5 7 nights min

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

Price per night from

$473

Price per night from

$473

21

41 Captains Walk 102234

Chatham / North Chatham

North Chatham house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$436

Price per night from

$436

(1) Excellent 

32

#602: Make memories in this Chatham beach home within steps to Nantucket Sound!

Chatham / South Chatham

South Chatham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$157

Price per night from

$157

(1) Excellent 

9

6065# Barre-Hammond House

Cape Cod / Chatham

Chatham house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children

Price per night from

$228

Price per night from

$228

(1) Excellent 

16

Captain's Haven

Chatham / West Chatham

West Chatham cottage

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$201

Price per night from

$201

12

4463 Levine

Cape Cod / Chatham

Chatham house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children

Price per night from

$157

Price per night from

$157

10

8219# Tobin

Cape Cod / Chatham

Chatham house

3 10 7 nights min

  • 3 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$250

Price per night from

$250

11

8112 Weller, Bruce

Chatham / South Chatham

South Chatham house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$214

Price per night from

$214

9

5815 Durr

Chatham / North Chatham

North Chatham house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$135

Price per night from

$135

(2) Excellent 

18

South Chatham Cape Cod Vacation Rental (1798)

Cape Cod / Chatham

Chatham house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$373

Price per night from

$373

15

8216 Shepard

Cape Cod / Chatham

Chatham house

5 9 7 nights min

  • 5 bedrooms
  • sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$429

Price per night from

$429

(5) Excellent 

19

All New Cottage in Chatham Near Hardings Beach

Cape Cod / Chatham

Chatham cottage

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Child Friendly
“Perfect cottage! A must stay!” The description did not disappoint, this cottage is just perfect! Everything was so clean, comfortable and beautiful we didn't want to leave. There was enough space for our family of four to relax in the living room or
…see more

Price per night from

$229

Price per night from

$229

17

8323 Gruffat

Cape Cod / Chatham

Chatham house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$414

Price per night from

$414

11

8033 Junda105

Chatham / North Chatham

North Chatham house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$571

Price per night from

$571

17

8032 Junda 95

Chatham / North Chatham

North Chatham house

5 11 7 nights min

  • 5 bedrooms
  • sleeps 11
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$571

Price per night from

$571

18

8285 Wieber/Cahill

Chatham / South Chatham

South Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$214

Price per night from

$214

10

4103 Davis, Judith

Cape Cod / Chatham

Chatham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$178

Price per night from

$178

12

62 PATUXET TRAIL 124579

Chatham / South Chatham

South Chatham cottage

3 5 7 nights min

  • 3 bedrooms
  • sleeps 5
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$107

Price per night from

$107

34

Cape Cod Dream Vacation Home

Chatham / North Chatham

North Chatham house

4 10 6 nights min

  • 4 bedrooms
  • sleeps 10
  • 6 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary

Price per night from

$862

Price per night from

$862

8

8045 Comis

Cape Cod / Chatham

Chatham house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$192

Price per night from

$192

15

West Chatham Cape Cod Waterfront Vacation Rental (20)

Cape Cod / Chatham

Chatham house

2 4 7 nights min

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

Price per night from

$187

Price per night from

$187

11

8095# Barre-Gilpin Ln

Chatham / West Chatham

West Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$500

Price per night from

$500

17

8250 Hofmann, K

Cape Cod / Chatham

Chatham house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$900

Price per night from

$900

10

8257 Collins, Lisa

Cape Cod / Chatham

Chatham house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$243

Price per night from

$243

(2) Excellent 

15

Chatham Cape Cod Vacation Rental (7102)

Cape Cod / Chatham

Chatham house

3 8 7 nights min

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

Price per night from

$345

Price per night from

$345

(3) Excellent 

23

Walk to Ridgevale Beach From Family Friendly Home

Chatham / West Chatham

West Chatham house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.6 mi
  • Child Friendly

Price per night from

$493

Price per night from

$493

(3) Very Good 

9

Chatham 1 Bedroom Beachfront Old Village

Cape Cod / Chatham

Chatham house

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Air conditioning
  • Private garden
“Wonderful Little Cottage on Mill Pond” My sister and I just got back from a 2 week stay at this lovely little cottage on Mill Pond. This is a small place - but very tastefully furnished and decorated with a nice layout. The kitchen had everything we
…see more

Price per night from

$287

Price per night from

$287

12

8374# Zippo

Chatham / South Chatham

South Chatham house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$114

Price per night from

$114

20

6876 Goslin

Cape Cod / Chatham

Chatham house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet Friendly

Price per night from

$539

Price per night from

$539

7

8057 Smith, Gordon

Chatham / South Chatham

South Chatham house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ask about children
  • Air conditioning

Price per night from

$164

Price per night from

$164

About Chatham

Located at the "elbow" of Cape Cod, Chatham has earned the reputation of a premier New England vacation spot. The area is known for its wide range of art galleries, beautiful beaches, and amazing views of the coast. In fact, this small town has been named one of America's Dozen Distinct Destinations by The National Trust for Historic Preservation. You'll find rows of art galleries and many unique boutique shops along Main Street, in addition to some of the best restaurants on the Cape like The Chatham Squire.

There's plenty to do outside of this strip as well, so be sure to make time for some of these must-see attractions and destinations:

  • Chatham Fish Pier: In addition to the great coast views, this pier offers great photo opportunities, especially of local fishermen unloading their catch for the day.
  • Chatham Lighthouse: Take one of the free tours of the lighthouse before climbing to the top of it yourself.
  • Watch the Seals: A few local business offer one-hour seal watching cruises.
  • Art Galleries: Chatham is home to over a dozen art galleries including the Chatham Art Gallery and the Potts Gallery of Fine Art.
  • Railroad Museum: This free museum gives visitors a look into the history of Cape Cod's former railroad industry.
  • Go to the Beach: Chatham is home to several great beaches, many of which are within walking distance of one another. Be sure to check out Chatham Lighthouse Beach.

Whether you're looking for a spacious home with a pool and high-end amenities, or a luxury condo just steps from the ocean and all the shopping and galleries Chatham has to offer, there's a vacation rental in the area that has everything you're looking for.