50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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South Chatham
42 properties
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27 properties
West Chatham
8 properties

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437 Vacation rentals

45

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

$1600 - $4495 / week

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Responds fast!
avg. 1 hour 41 minutes

from $275 / night

(3) Very Good 

9

Home rental in Chatham

Cape Cod / Chatham

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village. …see more

from $250 / night

$1500 / week

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from $250 / night

(1) Excellent 

41

Vacation home in Chatham

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
Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of q …see more

from $600 / night

$4000 - $5200 / week

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from $600 / night

21

Chatham Vacation home rental

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Enjoy the downtown location of this Cape Cod Vacation Rental Home in the village of Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,500-3,950/week. Convenient to Chatham shops, restaurants, new Orpheum movie theatre and Oyster …see more

from $343 / night

$2400 - $3951 / week

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from $343 / night

11

North Chatham Vacation home accommodation

Chatham / North Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball …see more

from $143 / night

$1000 - $1600 / week

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from $143 / night

31

Vacation home in Chatham

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
This quaint Cape home is located just minutes away from Harding's Beach, a beautiful and popular spot to spend the day soaking in the sun and sea. Situated along Bucks Creek Marsh and just a stone's throw from the Oyster River, this 3-bedroom home is a perfect mix of se …see more

from $99 / night

$800 - $2199 / week

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from $99 / night

24

Chatham Vacation home rental

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
Nestled in a private garden setting a delightful 3 bedroom / 1.5 bath home in Hardings Beach Hills is available to rent this season. With access to Buck's Creek flowing to Nantucket Sound, you can launch your kayak, fish or crab from the private association neighborhood …see more

from $243 / night

$1695 - $2195 / week

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from $243 / night

(4) Excellent 

19

Chatham Vacation cottage rental

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Welcome to our entirely renovated 'old Cape' cottage, with a sunny, open floor plan, brand new appliances and furnishings, washer/dryer and central air. After the beach, rinse off in the private outdoor shower before relaxing on the sunny patio. The Space: Create cheri …see more

from $200 / night

$1400 - $2300 / week

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from $200 / night

15

Vacation home in Chatham

Cape Cod / Chatham

3 12 7 nights min

  • 3 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rates ~~ In Season, $2900 per week, including the cleaning fee Off Season, $2200, including the cleaning fee Beautiful home built in 2006 with an airy open floor plan and tons of living space throughout. Great central location, close to all the shops and res …see more

from $286 / night

$2000 - $2700 / week

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from $286 / night

33

Chatham Vacation home rental

Cape Cod / Chatham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Featuring gorgeous gardens and outdoor spaces to explore, a luxurious and updated interior, and all the comforts of home, this beautiful rental has it all! Ideal for two guests, this would be a fantastic place for a honeymoon, couples getaway, or even a relaxing solo re …see more

from $99 / night

$693 / week

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Responds fast!
avg. 2 hours 15 minutes

from $99 / night

28

Vacation home in South Chatham

Chatham / South Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Welcome to Sea Mist! Spacious Cape Cod Beach House with Central AC and WiFi. Steps to the ocean with deeded access to private beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,000-$3,200/week. Special deal $1275 off season! Relax …see more

from $375 / night

$1475 - $33000 / week

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from $375 / night

24

Vacation home rental

Chatham / South Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Pet friendly
#602 Port View Home: Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view h …see more

from $150 / night

$1199 - $3499 / week

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from $150 / night

46

Chatham Vacation home rental

Cape Cod / Chatham

5 14 7 nights min

  • 5 bedrooms
  • Sleeps 14
  • 7 nights min
  • Child friendly
  • Air conditioning
Privacy and tranquility are enjoyed at this stunning in-town estate setting! 5 bedrooms (sleeps 14), Central AC, WiFi, and 3 levels of living space all make for a dream vacation in the heart of Chatham.​ Walk to beach and town! Peak Summer Weekly Rates:  last week of Ju …see more

from $643 / night

$4500 - $8500 / week

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from $643 / night

(20) Excellent 

48

Vacation home in Chatham

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
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

$1600 - $4495 / week

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Responds fast!
avg. 39 minutes

from $275 / night

11

Vacation home in North Chatham

Chatham / North Chatham

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $5350 per week, INCLUDING linens & cleaning! ~~ Off-Season: $4900 per week including linens & cleaning! Weekly rentals from mid-JUNE to mid-SEPT Gorgeous home in secluded North Chatham neighborhood. The home features hardwood floors, WiFi and central a …see more

from $643 / night

$4500 - $4950 / week

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from $643 / night

24

Vacation home in North Chatham

Chatham / North Chatham

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Come stay at: Misty Meadow! Completely renovated vacation condo on Cape Cod in North Chatham. Enjoy this lovely condo with all amenities including Central A/C mini splits, wifi, and everything new. Peak Summer Weekly Rates:  last week of June until the first week in Sep …see more

from $122 / night

$850 - $1275 / week

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from $122 / night

17

Chatham Vacation home rental

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rates: $4425 per week, including cleaning Off-Season: $3125 per week cleaning Weekly rentals from mid-JUNE to mid-SEPT Stunning, new home located on Oyster River with breathtaking views of the river and marsh. Enjoy your afternoons after the beach watching t …see more

from $415 / night

$2900 - $4200 / week

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from $415 / night

29

Vacation home in Chatham

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Great location! Oyster Pond & Chatham Village!! At this home you will be just apprx. 500 ft to private Oyster Pond access, 7/10ths of a mile to the the public beach at Oyster Pond and just 6/10ths of a mile to Chatham Village at Cross St. This fantastic home features p …see more

from $333 / night

$2325 - $3475 / week

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from $333 / night

20

Chatham Vacation home rental

Cape Cod / Chatham

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $10,400 per week, including the cleaning fee ~~ Off Season: $7,400 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Fabulous new home close to downtown Chatham! This gorgeous house is located on a quiet street, but is also …see more

from $1000 / night

$7000 - $10000 / week

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from $1000 / night

13

Chatham Vacation home rental

Cape Cod / Chatham

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Child friendly
  • Car not necessary
NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. …see more

from $422 / night

$2950 - $3200 / week

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from $422 / night

13

Home rental in Chatham

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to: Cape Cranberry! Quintessential Cape Cod Vacation Rental Cottage in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $1,400/week. Enjoy this Cape Cod beach cottage with casual coastal dec …see more

from $150 / night

$1050 - $1400 / week

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from $150 / night

25

Vacation home in Chatham

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to Sea Glass! This Cape Cod Vacation Rental home is just .2 miles from Pleasant Street Beach in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,900/week. Warm water, sunsets, and miles of beach on Nantucket Sound await …see more

from $279 / night

$1950 - $2900 / week

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from $279 / night

33

Vacation home in Chatham

Cape Cod / Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Welcome to: Endless Summer. Views-Views-Views! Pet Friendly Cape Cod Vacation Rental home with rooftop deck is just .2 to Ridgevale Beach. Peak Summer Weekly Rates:  (last week of June until the first week in September) $4,050/week Pet friendly! Enjoy water views from t …see more

from $400 / night

$2750 - $4050 / week

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from $400 / night

28

Vacation home in South Chatham

Chatham / South Chatham

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Air conditioning
Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2000-$2,600 A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0. …see more

from $286 / night

$2000 - $3400 / week

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from $286 / night

18

Home rental in Chatham with shared pool

Cape Cod / Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
2017 Rental Rate: $6250 per week, including the cleaning fee Off-Season $4450 per week, including the cleaning fee The perfect place for a most memorable and rewarding vacation. New owners of this original Morris Island home have brought in all new furnishings and bed s …see more

from $600 / night

$4200 - $6000 / week

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from $600 / night

32

Vacation home in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Walk to Hardings Beach- Central air - private! Peak Summer Weekly Rates:  last week of June until the first week in September: $1800-$2,200/week. Ranch-style home with Central air-comfortable, easy living all on one floor! 3 Bedrooms, 2 baths, sleeps 6 with central air, …see more

from $243 / night

$1700 - $2200 / week

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from $243 / night

47

Chatham Vacation home rental

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
ON THE WATER ... * Beautiful water views! * Back decks open to mesmerizing views of Emery Pond * Hammock and patio furniture chosen for comfort and relaxation! * Direct access to pond from backyard. * Clean swimmable pond. * Bass fishing pl …see more

from $475 / night

$2900 / week

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from $475 / night

31

Vacation home in Chatham

Cape Cod / Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Comfortable 3 bedroom, 2 bath quiet summer retreat only a half mile to downtown Chatham! Peak Summer Weekly Rates:  last week of June until the first week in September: $1900-$2,000/week. Offering Central AC & Wifi - like most of our Cape Cod Vacation Home Rentals - wit …see more

from $300 / night

$1250 - $2000 / week

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from $300 / night

22

Vacation home in Chatham

Cape Cod / Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Come Stay at: The Crow's Nest! Pet Friendly! Spend Lazy summer days at this Cape Cod Vacation rental in Chatham. Peak Summer Weekly Rates:  last week of June until the first week in September: $3,400/week. With the shade from the pines, the spray of sea salt from the Na …see more

from $500 / night

$2500 - $3400 / week

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from $500 / night

(1) Excellent 

51

Vacation home in Chatham

Cape Cod / Chatham

9 20 Min stay varies

  • 9 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Come Stay at: The Priscilla House! Pet Friendly! The Priscilla House is a lovely vacation rental home nestled on Main Street in the charming town of Chatham, Massachusetts on Cape Cod. Walk to town and Lighthouse beach! Sheets and Towels INCLUDED! Peak Summer Weekly Rat …see more

from $1500 / night

$9000 - $15000 / week

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from $1500 / night

(2) Excellent 

34

Vacation home in South Chatham

Chatham / South Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Lovingly renovated in winter 2013 and designed by a New York couple, this 4-bedroom, 3-bathroom colonial saltbox home evokes the style and taste of classic Americana, decorated with vintage finds and unique antique pieces. Whether you’re on a family vacation, couples ge …see more

from $260 / night

$1700 - $2900 / week

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Responds fast!
avg. 1 hour 45 minutes

from $260 / night

(2) Excellent 

52

Vacation home rental

Chatham / North Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience "The Salty Dog". Luxury at its finest. This 4,000 square foot, pet friendly, waterfront 4 bedroom/4 bath home sleeps 10. You will find Central Air, WiFi, linens, and all amenities at this Chatham Vacation Rental Home, everything for a great Cape Cod Vacation! …see more

from $1900 / night

$7500 - $12000 / week

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from $1900 / night

15

Chatham Vacation home rental

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $2150 per week, including the cleaning fee Off-Season: $1525 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious three bedroom ranch in quiet neighborhood near Hardings Beach. Recently updated, it is filled with comfo …see more

from $193 / night

$1350 - $1976 / week

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from $193 / night

13

Vacation home in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $1975 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning fee Enjoy the simple life in this classic, Chatham cottage. Located in the popular Hardings Hills neighborhood, a quick walk down to Hardings Beach! The newly …see more

from $143 / night

$1000 - $1800 / week

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from $143 / night

29

Vacation home rental

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
This landmark property has the most remarkable views anywhere! After a day at the beach relax and take in one of the prettiest views on the Cape. Three bedrooms, one full and two half baths and on a quiet cul-de-sac, at the very end of the road and sitting on just over …see more

from $643 / night

$4500 / week

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from $643 / night

32

Vacation home in Chatham

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to The Cape Escape! Walk to Hardings Beach from this Chatham Vacation Rental Home. 4 Bedrooms, sleeps 8. Access to association dock and picnic area in Harding's Hills Association.  A/C units in 3 bedrooms and the main living area- there is cable and Wifi too.​ P …see more

from $186 / night

$1300 - $2900 / week

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from $186 / night

12

South Chatham Vacation home rental

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
2017 Rental Rate: $2775 per week, including the cleaning fee Off-Season: $1175 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Lovely, updated condo with water-views of the Nantucket Sound. Light and bright with comfy upscale furnishings. Locat …see more

from $143 / night

$1000 - $2600 / week

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from $143 / night

23

Home rental in Chatham

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home is only 0.3 miles to Ridgevale Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,800/week. This home has window AC units in the upstairs bedrooms as well as t …see more

from $215 / night

$1500 - $2800 / week

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from $215 / night

28

Chatham Vacation home rental

Cape Cod / Chatham

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
Come Stay at: Chatterbox! Location! Location! Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,000 - $4,200/week. Whether you e …see more

from $375 / night

$2275 - $4200 / week

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from $375 / night

12

Vacation home in Chatham

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It h …see more

from $179 / night

$1250 - $1800 / week

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from $179 / night