40 Best Vacation Rentals in South Chatham - Holiday Lettings - Cabins

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2,669 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

$1,600 - $5,250 / week

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Responds fast!
avg. 1 hour 22 minutes

from $275 / 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. Relax and unwind at this 3 bedroom, 2 bath home in Chatham sleeping 6. Enjoy the decks, outdoor shower, and especially the hot tub! Light …see more

from $375 / night

$1,475 - $3,300 / week

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from $375 / night

22

South Chatham Vacation home rental

Chatham / South Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
This 4 bedroom, 2.5 bathroom home in South Chatham has plenty of space inside and out. There is a sunken dining room off the main living room that opens to a furnished patio with gas grill. A second living space on the lower level has a TV, foosball table, half-bath, …see more

from $415 / night

$2,900 / week

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from $415 / night

(1) Excellent 

26

Vacation home rental

Chatham / South Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
*Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. …see more

from $179 / night

$1,418 - $3,499 / week

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from $179 / night

12

Vacation home in South Chatham

Chatham / South Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $1675 per week, including the cleaning fee Off-Season: $975 per week, including the cleaning fee Light and bright 4 bedroom home on quiet cul-de-sac in South Chatham. Comfortable furnishings throughout. Large upstairs bedrooms offer extra seating space …see more

from $114 / night

$800 - $1,500 / week

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from $114 / night

17

Vacation home rental

Chatham / South Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four b …see more

from $429 / night

$3,000 / week

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from $429 / night

21

Vacation cottage rental

Chatham / South Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, …see more

from $186 / night

$1,300 / week

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from $186 / night

14

Vacation home in South Chatham

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Charming 3 bedroom, 1 bath cottage with views of Nantucket Sound from the rooftop deck. Forest Beach is just 2/10ths of a mile away. Amenities include a window AC unit in each bedroom, Wi-Fi, cable TV with basic cable only, DVD player, washer, enclosed outdoor shower, a …see more

from $229 / night

$1,600 / week

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from $229 / night

17

Vacation cottage in South Chatham

Chatham / South Chatham

1 2 5 nights min

  • 1 bedroom
  • Sleeps 2
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Yes, the price is low but that's why so many customers have come for decades! So wanting for a nice clean quiet apartment unit close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant …see more

from $65 / night

$455 / week

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from $65 / night

15

Home rental in South Chatham

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
There's a path to Pleasant Street Beach just down from this 3 bedroom 2 bathroom cottage. Enjoy a day at the beach and return to relax on the back deck with dining table and both gas and charcoal grills. The kitchen has been beautifully updated with stainless steel ap …see more

from $315 / night

$2,200 / week

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from $315 / night

9

Vacation cottage in South Chatham

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
19 Glendon Way, S. Chatham Casual knotty pine summer cottage just 1/2 mile to Pleasant Street Beach. This 3BR/1BA single level cottage is located in a nice quiet neighborhood of South Chatham. Convenient to shopping - just a 10 minute drive into town. $1000 per week * …see more

from $129 / night

$900 - $1,000 / week

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from $129 / night

14

Vacation home in South Chatham

Chatham / South Chatham

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Air conditioning
Come enjoy our spacious 3-bedroom, 2.5 baths home that is just a short walk to Forest Beach and the warm waters of Nantucket Sound. Our home is located on a quiet lane 0.4 mile to the beach, 0.5 to the Cape Cod bike trail, and less than 4 miles to shopping and eating in …see more

from $329 / night

$2,300 / week

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from $329 / night

7

South Chatham Vacation home rental

Chatham / South Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $1675 per week including the cleaning fee. This is a FRIDAY TO FRIDAY RENTAL. ~~ Off-Season: $1275 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Adorable, updated rental located on a quiet street in South Chatham. New fur …see more

from $157 / night

$1,100 - $1,500 / week

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from $157 / night

32

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) Peak Summer Weekly Rates: $7,400 - $8,900 Rents Saturday to Saturday during peak season Be among the first to vacation at this wonderful custom-built home in South Chatham. Just finish …see more

from $828 / night

$5,800 - $8,900 / week

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from $828 / night

12

South Chatham Vacation home rental

Chatham / South Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate: $3175 per week, including the cleaning fee No Off-Season Recently renovated three bedroom home with beautiful views of Red River Marsh and Nantucket Sound! Filled with new furnishings and appliances, this spacious home offers central air, and a huge de …see more

from $429 / night

$3,000 / week

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from $429 / night

(2) Excellent 

21

Vacation home in South Chatham

Chatham / South Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Great views of Nantucket Sound from this 3 bedroom, 2.5 bathroom Chatham cottage. This is a newer house with multiple furnished decks and balconies as well as a covered porch and is just a stones throw to a semi-private beach on Nantucket Sound. The master bedroom is …see more

from $558 / night

$3,900 / week

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from $558 / night

24

Vacation home in South Chatham

Chatham / South Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Welcome to Forest Beach Cottage. This Cape Cod Vacation home rental in Chatham is just yards out of the back door to Forest Beach.   Central AC for those hot summer nights. You can smell the salt water from this ranch-style home with four bedrooms, two baths, and an ou …see more

from $429 / night

$3,000 / week

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from $429 / night

26

Vacation home in South Chatham

Chatham / South Chatham

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
2 BR, 1 Bath newly renovated walk/bike to beach and restaurants Renovated in 2017. Our Chatham home is walking/biking distance (0.7 miles) to Forest Beach, Cockle Cove Beach and Pleasant Beach, churches, restaurants, library and the Cape Cod Bike Trail, making it an id …see more

from $200 / night

$2,100 / week

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from $200 / night

16

Vacation home in South Chatham

Chatham / South Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rates: $2600 including the cleaning fee. Off-Season: $1600 including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Wonderful, light and bright summer home located just steps from Taylor's Pond, the Eel River and the warm waters of the Nantucket S …see more

from $200 / night

$1,400 - $2,400 / week

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from $200 / night

17

Vacation home in South Chatham

Chatham / South Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopp …see more

from $422 / night

$2,950 - $3,200 / week

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from $422 / night

(2) Very Good 

14

Vacation home in South Chatham

Chatham / South Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Enjoy your Chatham vacation in this 3 bedroom, 2 bathroom house that is only 2/10th of a mile from Pleasant Street Beach on Nantucket Sound. This traditional Cape home features 2 bedrooms on the first floor and 2 bedrooms on the 2nd floor. The living room and kitchen …see more

from $272 / night

$1,900 / week

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from $272 / night

12

South Chatham Vacation home rental

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Our highly rated & reviewed 3 bedroom 1 & 1/2 bath home is nestled on a quiet side street just 3/10 tenths of a mile from one of the best beaches in Chatham...Forest Beach. Our comfortable home is 1100 square feet; and is updated & modern with Air Conditioning, Wi-Fi …see more

from $279 / night

$1,950 / week

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from $279 / night

30

Vacation home in South Chatham

Chatham / South Chatham

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
Welcome to Summer Oasis! Newer Custom Cape Cod Vacation Rental home that is walk to beach in Chatham sleeping 9.   A walk for most to Cockle Cove Beach at the end of the street on the Nantucket Sound (0.6 mile)! Central air, free WiFi, a screened in porch, 3 spacious b …see more

from $286 / night

$2,000 - $3,400 / week

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from $286 / night

(2) Excellent 

25

Vacation home in South Chatham

Chatham / South Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Begin your Cape Cod adventure by staying in this beautiful 4-bedroom, 3-bathroom saltbox home. Surrounded by natural beauty and close to everything the Cape has to offer, this home is a perfect choice for a group of friends traveling together or a family getaway. Your …see more

from $260 / night

$1,820 - $2,975 / week

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Responds fast!
avg. 2 hours 47 minutes

from $260 / night

30

Vacation home in South Chatham

Chatham / South Chatham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house h …see more

from $350 / night

$2,450 / week

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from $350 / night

(1) Excellent 

9

Vacation cottage in South Chatham

Chatham / South Chatham

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Sho …see more

from $89 / night

$630 - $714 / week

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from $89 / night

30

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 $308 / night

$2,150 / week

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from $308 / night

24

Home rental in South Chatham

Chatham / South Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
*Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. …see more

from $179 / night

$1,256 - $3,100 / week

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from $179 / night

(2) Excellent 

14

South Chatham Vacation cottage rental

Chatham / South Chatham

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Yes, the price is low but that's why so many customers have come for decades! Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining? Well, then...Pleasant Forest Shor …see more

from $100 / night

$700 - $868 / week

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from $100 / 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
2018 Rental Rate: $3625 per week, including the cleaning fee Off-Season: $2525 per week, including the cleaning fee Wonderful waterfront home, right on Taylor's Pond! This spacious home is light and bright, filled with upscale furnishings, colorful decor, and offers a p …see more

from $329 / night

$2,300 - $3,400 / week

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from $329 / night

11

Home rental in South Chatham

Chatham / South Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $3000 per week including the cleaning fee Off-Season Fabulous Cape Cod beach rental located steps from Nantucket Sound with breathtaking views from the huge deck overlooking the marsh and the ocean. Airy, light and bright decor. Finished walkout lower …see more

from $271 / night

$1,900 - $2,800 / week

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from $271 / night

13

Vacation cottage rental

Chatham / South Chatham

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
62 PATUXET TRAIL Sweet cottage close to Cockle Cove Beach in South Chatham. Sleeps 5. First bedroom 1 Double, 2nd bedroom 2 twins, 3rd bedroom 1 twin. $950 off season and $1200 in season * $100 Handling Fee * choice of $55 Damage Insurance or $350 Security Deposit Plea …see more

from $108 / night

$750 - $1,200 / week

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from $108 / night

18

Home rental in South Chatham

Chatham / South Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate ~ $2050 per week, including the cleaning fee Off-Season: $1750 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Spacious 4 BR home on quiet street near Cockle Cove Beach. Lots of living space in this private and centrally lo …see more

from $214 / night

$1,500 - $1,800 / week

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from $214 / night

28

South Chatham Vacation home rental

Chatham / South Chatham

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Book your stay at this updated and spacious 3-bedroom, 2.5-bathroom vacation rental house in the heart of Cape Cod’s best town, South Chatham. Boasting 2,688 square feet of tasteful living space, an outdoor fire pit with ample seating, a wet bar, 2 gas grills and picnic …see more

from $320 / night

$2,240 - $2,835 / week

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Responds fast!
avg. 2 hours 55 minutes

from $320 / night

(1) Excellent 

24

Vacation cottage in South Chatham

Chatham / South Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
0.1 mile from a popular summer Nantucket Sound beach… can walk or ride or /access to private beach via path along marsh just steps away from the house quiet family area… ranch / cottage style house with summer beach flavor with views of Taylor Pond 1 bathroom / eat in …see more

from $268 / night

$1,875 / week

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from $268 / night

(1) Excellent 

15

Vacation home in South Chatham

Chatham / South Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
15 Bobbies Lane CHATHAM Charming and Updated Cottage in South Chatham! A/C, convenient to shopping, beaches, town tennis and golf. Only 1/2 mile to Nantucket Sound. Screened in Porch, WiFi, 1 Queen, 2 singles and 2 Queen Sofa beds. Sleeps 6. $1250 per week * $100 Ha …see more

from $115 / night

$800 - $1,250 / week

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from $115 / night

9

South Chatham Vacation home rental

Chatham / South Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
This newly listed, cozy Chatham cottage is just steps away from the Old Colony Rail Trail. There are two bedrooms, one with a double sized bed and a/c unit, and the second with two twins. There is also a full bath with tub/shower combination. This cute cottage features …see more

from $136 / night

$950 - $1,150 / week

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from $136 / night

11

Vacation home in South Chatham

Chatham / South Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Conveniently located in South Chatham, this lovely Townhouse is close to some of Chatham's best swimming beaches. A quick drive in either direction can transport you off to the quaint villages of Chatham or Harwichport for some of the Cape's best dining and shopping. …see more

from $108 / night

$750 - $1,050 / week

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from $108 / night

12

Vacation home in South Chatham

Chatham / South Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $1700 per week, including the cleaning fee Off Season: $1150, including the cleaning fee Charming and updated ranch, located in a quiet neighborhood but is also a quick drive to the warm waters of Cockle Cove Beach! This light and bright ranch, feature …see more

from $142 / night

$1,000 - $1,550 / week

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from $142 / night

15

Vacation home in South Chatham

Chatham / South Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Perfect for a relaxing vacation. Located in a quiet location in South Chatham, only ½ mile to Nantucket Sound. This cute and cozy cottage with central air has 2 bedrooms, one with a queen sized bed and the second with 2 twins and two separate living spaces for family co …see more

from $115 / night

$800 - $1,250 / week

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from $115 / night