50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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South Chatham
42 properties
North Chatham
28 properties
West Chatham
10 properties

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443 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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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

$2200 / week

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from $415 / 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

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 - $2650 / week

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from $150 / 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

(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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from $275 / night

28

Chatham Vacation home rental

Cape Cod / Chatham

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Plea …see more

from $500 / night

$3500 - $8500 / week

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from $500 / night

30

Vacation home in South Chatham

Chatham / South Chatham

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Brand new custom built beauty in South Chatham with water views (linens included) NEW Listing for 2017! (More photos to come soon!) Peak Summer Weekly Rates: $6,400 - $7,300 (Rents Saturday to Saturday during peak season) Be among the first to vacation at this wonderful …see more

from $729 / night

$5100 - $7300 / week

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from $729 / 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 - $2200 / week

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from $200 / night

29

Vacation home in Chatham

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Welcome to: Seaside Stroll! Beachfront Condo! 3 Bedrooms, sleeps 6! Enjoy water views from both upstairs and main level decks. Walk down the path to the Outermost Harbor, Little Beach, or bike up to the village of Chatham. Easy bike ride to Lighthouse Beach and Monomoy …see more

from $300 / night

$1500 - $2400 / week

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from $300 / night

38

Vacation home rental

Chatham / West Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
​Enjoy Family Tides, this pet friendly, updated, 4 bedroom home sleeps 10. Walk to Harding's Beach with deck and outdoor shower. A/C units. Wifi too. Peak Summer Weekly Rates:  (last week of June until the first week in September) $2000-$2,600 Walk to Harding's Beach fr …see more

from $198 / night

$1375 - $2600 / week

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from $198 / night

9

Chatham Vacation home rental

Cape Cod / Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Brand new custom built beauty in Chatham, walk to Ridgevale Beach! (linens included) NEW Listing for 2017! (More photos to come soon!) Peak Summer Weekly Rates: $5,200 - $5,800 (Rents Saturday to Saturday during peak season) This brand new custom home will  provide a lu …see more

from $572 / night

$4000 - $5800 / week

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from $572 / night

26

Vacation home in North Chatham

Chatham / North Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
Beautiful Home in North Chatham! This light filled, spacious and comfortable home in North Chatham is a perfect spot for your Cape Cod vacation! Located on a large lot with a fantastic patio, you will enjoy outdoor living as well as the beautiful interior. Close to C …see more

from $543 / night

$3800 / week

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from $543 / 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

21

Vacation apartment in Chatham

Cape Cod / Chatham

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Air conditioning
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this tra …see more

from $300 / night

$2100 - $2450 / week

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from $300 / night

35

Home rental in Chatham

Cape Cod / Chatham

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Child friendly
Immaculate Chatham Village Renovation, Walk to Beach & Village Peak Summer Weekly Rates: $7,900-$8,800 (Linens Included) (Rents Saturday to Saturday during peak season) Your quintessential Chatham vacation awaits! This masterfully restored classic is situated in the hea …see more

from $572 / night

$4000 - $8800 / week

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from $572 / night

11

Vacation home in North Chatham

Chatham / North Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $2825 per week including the cleaning fee ~~~ Off-Season: $2225 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from …see more

from $286 / night

$2000 - $2600 / week

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from $286 / night

11

Home rental in Chatham

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $2575 per week, with the cleaning fee~~~~Off-Season: $1775 per week, with the cleaning fee~~ Weekly rentals from mid-JUNE to mid-SEPT Updated, light & bright home located about 1/2 mile from downtown Chatham & Oyster Pond. New kitchen and furnishings t …see more

from $229 / night

$1600 - $2400 / week

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from $229 / night

27

Chatham Vacation home rental

Cape Cod / Chatham

4 12 7 nights min

  • 4 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Ask about pets
This perfectly situated Chatham rental is welcoming to you and your four legged friends. Located close to Shore Road, you and your guests will enjoy the best of being close to the water and close to Main Street. Walk to town on sidewalks and enjoy the amazing shops and …see more

from $772 / night

$5400 - $6800 / week

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from $772 / 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
  • Ask about pets
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

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 $415 / night

$2200 / week

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from $415 / night

21

Vacation home in North Chatham

Chatham / North Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 mile to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 2 miles to Main St …see more

from $286 / night

$2000 - $3050 / week

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from $286 / night

26

Home rental in North Chatham

Chatham / North Chatham

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Completely renovated condo in North Chatham. Enjoy this lovely condo with all amenities including Central AC mini split, WiFi, and new furnishings. Sleeps 4. Read on to learn more about our Chatham Mass Vacation Rentals Peak Summer Weekly Rates:  last week of June until …see more

from $122 / night

$850 - $1275 / week

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from $122 / night

10

Chatham Vacation condo rental

Cape Cod / Chatham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
RENOVATED very bright, beachy condo, 2bdrms/2bths. This unit comes equipped with AC, fully stocked kitchen and 2 decks to enjoy your wine/coffee. The decks overlook Little Mill Pound. This condo is located in town and the famed, kid friendly Oyster Beach & Lightho …see more

from $260 / night

$1900 - $2500 / week

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from $260 / night

(1) Excellent 

28

Vacation home rental

Cape Cod / Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Coastal, seaside home offering Central air has plenty of room for 3 couples or 2 families. Walk to beach and town! Peak Summer Weekly Rates:  last week of June until the first week in September: $3,100/week. This Cape Cod Vacation Rental in Chatham has an open floor pla …see more

from $208 / night

$1450 - $3101 / week

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from $208 / night

12

Vacation home in West Chatham

Chatham / West Chatham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Ask about children
  • Air conditioning
Enjoy this updated 2 bedroom, 1 bath Chatham vacation cottage with views of Oyster River. The open kitchen, dining and living room has a slider leading out to a large deck with chaise lounges, dining table with umbrella, gas grill and enclosed outside shower. Amenities …see more

Pricing unknown

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Pricing unknown

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

(1) Excellent 

29

Home rental in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
WATERFRONT! Come stay at: Milhaven, This Cape Cod Vacation Rental is located in Chatham's Old Village and is right on Mill Pond. Peak Summer Weekly Rates:  last week of June until the first week in September: $2,500 - $3,900/week. The Old Village is popular for its hist …see more

from $358 / night

$2500 - $3900 / week

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from $358 / night

9

Chatham Vacation home rental

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $2100 per week, with the cleaning fee ~~No Off-Season~~ Welcome!! This roomy Cape sits up on a hill located just off of Cockle Cove Road on a quiet one way drive. Just .4 mi to Cockle Cove Beach. There are three bedrooms and 2 full and one half baths. …see more

from $279 / night

$1950 / week

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from $279 / night

26

Home rental in Chatham

Cape Cod / Chatham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Chatham Village Classic, Behind Lighthouse (Pets Considered) Peak Summer Rates: $5,300 - $5,500 (Rents Saturday to Saturday during peak season) This grand Chatham Village family home is located in Chatham, right near the Lighthouse.This vintage antique house has 5 bedro …see more

from $386 / night

$2700 - $5500 / week

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from $386 / night

28

Vacation home rental

Chatham / South Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This rental is a comfortable 3 bedroom, 2 bath that sleeps 8. It sits on a pretty lot with a big backyard just 7/10th of a mile to Forest Beach in Chatham. A sunporch off the kitchen is great for that morning cup of coffee and the large deck has a gas grill for evening …see more

from $286 / night

$2000 / week

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from $286 / night

31

Vacation home in North Chatham

Chatham / North Chatham

7 24 Min stay varies

  • 7 bedrooms
  • Sleeps 24
  • Min stay varies
  • Child friendly
Historic North Chatham Estate. Sleeps 20, private beach! (linens included) NEW Listing for 2017! Peak Summer Weekly Rates: $13,900 - $16,900 JUST REDUCED -- Remaining Peak Week reduced $1,000/week! (Rents Saturday to Saturday during peak season) "Shore Acres", an extra- …see more

from $1100 / night

$8900 - $16900 / week

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from $1100 / night

11

Vacation home in North Chatham

Chatham / North Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $3625 per week, including the cleaning fee ~~~~~Off-Season: $2525 with cleaning fee included ~~~~~ Fabulous updated home located in North Chatham, convenient to town and many of Chatham's beaches! High ceilings & hardwood floors throughout and a screen …see more

from $329 / night

$2300 - $3400 / week

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from $329 / night

11

Vacation home in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $2475 per week including the cleaning fee ~~ Off Season: $1775 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming year-round home, with central air conditioning, within walking distance to the warm waters of popular R …see more

from $229 / night

$1600 - $2300 / week

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from $229 / 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
  • Ask about pets
2017 Rental Rate: $2175 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 - $2000 / week

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from $143 / night

29

Vacation home in Chatham

Cape Cod / Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $450 / night

$2325 - $3475 / week

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from $450 / night

16

Vacation cottage in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Pet friendly
Price Range $1100 - $1300. BOOK BEFORE JUNE FOR $1100 WEEKLY! THAT'S $200 OFF THE REGULAR RATE! NEW LISTING! AFFORDABLE DREAM BEACH HOUSE IN CHATHAM WITH LARGE FRONT AND BACK DECKS, ROOM FOR 6, AND ONLY STEPS TO FOREST BEACH! PET FRIENDLY! There is a dreamlike quality …see more

from $158 / night

$1100 - $1300 / week

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from $158 / night

13

North Chatham Vacation home rental

Chatham / North Chatham

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 rental Rate: $7850 including the cleaning fee~~ Off-Season: $3900 per week, including the cleaning fee ~ For 10 people only, lower level not available for Off-Season rentals~~ A large recently renovated 6 bedroom home located in the exclusive Cannon Hill Estates of …see more

from $500 / night

$3500 - $7450 / week

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from $500 / night

11

Chatham Vacation home rental

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $3275 per week, including the cleaning fee Off Season: $1475 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. This home is 1/2 mile from th …see more

from $186 / night

$1300 - $3101 / week

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from $186 / night

15

Home rental in South Chatham

Chatham / South Chatham

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
2017 Rental Rate: $3625 per week, including the cleaning fee No Off-Season Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and offers a private, peaceful setting in South Chatham …see more

from $486 / night

$3400 / week

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from $486 / night

1