50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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South Chatham
37 properties
West Chatham
8 properties

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2,395 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 - $4,495 / week

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Responds fast!
avg. 2 hours 19 minutes

from $275 / night

(1) Very Good 

11

Home rental in Chatham

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Charming, waterview condo in Old Chatham Village directly across from Lighthouse Beach and just a short walk to downtown Chatham. This two bedroom, one bathroom, 2nd floor condo has expansive views of Chatham Harbor, South Beach and the Atlantic Ocean. Recently renova …see more

from $336 / night

$2,350 / week

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from $336 / night

(1) Excellent 

16

Vacation cottage with golf nearby in West Chatham

Chatham / West Chatham

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
An old-fashion Cape vacation set in a secluded village of quaint, privately owned cottages on 4 acres of pine forest located on White Pond. This true Cape cottage is ideal for a couple or a small family. It has a complete kitchen/ living area with a pull out sofa bed, o …see more

from $175 / night

$950 / week

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from $175 / night

19

Home rental in Chatham

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This 3 bedroom, 2 bath house is located just .5 miles from Pleasant Street Beach and Red River Beach. This traditional Cape home has one bedroom with full bed and a full bathroom on the first floor and two bedrooms (king and two twins) and a full bath on the second flo …see more

from $243 / night

$1,700 / week

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from $243 / 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

16

Chatham Vacation home rental

Cape Cod / Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Just a mile from downtown Chatham, this 4 bedroom, 3 bathroom rental has all the comforts of home. The master bedroom with queen bed and a second bedroom with 2 twins are located on the 1st floor. The other two bedrooms and a bathroom are located on the second floor. …see more

from $386 / night

$2,700 / week

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from $386 / night

11

Vacation home in North Chatham

Chatham / North Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate: $2825 per week including the cleaning fee ~~~ Off-Season: $2225 per week including the cleaning fee Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to Cow Yard Landi …see more

from $285 / night

$2,000 - $2,600 / week

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from $285 / night

26

Vacation home in Chatham

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Newly Remodeled, One Mile to Chatham Village, 4 Minute Drive to Beach Peak Summer Weekly Rates: $3,125 - $3,825 Rents Saturday to Saturday during peak season Linens Included This newly remodeled home is conveniently located less than a mile from Chatham Village and s …see more

from $300 / night

$2,100 - $3,825 / week

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from $300 / night

39

North Chatham Vacation home rental

Chatham / North Chatham

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Pet friendly
Chatham Family Compound Sleeps 16   Walk to Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900  Rents Saturday - Saturday during peak season   Please click on the "Virtual Tour" to see a 3D tour of the home Welcome to sublime summer living at the Chatha …see more

from $785 / night

$5,200 - $13,900 / week

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from $785 / night

14

Chatham Vacation home rental

Cape Cod / Chatham

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning
$2,000 01/01 - 06/08 $2,400 06/09 - 06/22 $3,000 06/23 - 07/20 $3,400 07/21 - 08/24 $3,000 08/25 - 08/31 $2,400 09/01 - 09/14 $2,000 09/15 - 12/31 This recently renovated and fully updated 4 bedroom, 2 bathroom Chatham vacation rental is loc …see more

from $486 / night

$3,400 / week

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from $486 / night

20

Chatham Vacation home rental

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your …see more

from $322 / night

$2,250 - $3,000 / week

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from $322 / night

5

Chatham Vacation home rental

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate: $1800 per week, including the cleaning fee ----Off Season: $1000 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Cute 3 bedroom ranch, walking distance to town and Oyster Pond. A great new 2nd family room just finished in …see more

from $117 / night

$825 - $1,650 / week

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from $117 / night

34

Vacation home in North Chatham

Chatham / North Chatham

4 10 6 nights min

  • 4 bedrooms
  • Sleeps 10
  • 6 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. …see more

from $750 / night

$5,000 / week

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from $750 / night

(16) Very Good 

14

Vacation cottage rental

Cape Cod / Chatham

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Ask about children
At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham c …see more

from $105 / night

$695 - $995 / week

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Responds fast!
avg. 2 hours 8 minutes

from $105 / night

(1) Excellent 

23

Vacation home in Chatham

Cape Cod / Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Located on the Stage Harbor ?loop', this very private, quintessential Chatham 4-acre retreat has been recently renovated and has all new furnishings and amenities. The home is surrounded by mature plantings and conservation land and has views of Stage Harbor from the s …see more

from $700 / night

$4,900 / week

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from $700 / night

(1) Excellent 

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
This bright 3 bedroom, 2 bathroom Chatham rental home is situated only 2/10ths of a mile from popular Ridgevale Beach. This newer home is nicely appointed and well kept with hardwood floors throughout. The living room, dining area and kitchen are complemented by a comf …see more

from $458 / night

$3,200 / week

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from $458 / night

(1) Excellent 

24

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 $199 / night

$1,575 - $3,499 / week

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Responds fast!
avg. 3 hours 38 minutes

from $199 / night

(1) Excellent 

23

West Chatham Vacation home rental

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
This bright and airy family-friendly home is just a 1/2 mile walk to this fabulous sandy beach where you can enjoy swimming both on Nantucket Sound or in the milder waters in the adjoining tidal creek. Ridgevale Beach is one of Chatham's most popular destinations for va …see more

from $450 / night

$3,000 / week

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from $450 / night

20

Vacation home in Chatham

Cape Cod / Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
This spacious 3 bedroom, 3 bathroom home has plenty of gathering space both inside and out. Inside you will find vaulted ceilings in the living room, a sunroom and a finished lower level with ample seating and flat screen TV. The beautifully landscaped yard, complemen …see more

from $429 / night

$3,000 / week

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from $429 / night

(1) Excellent 

21

Vacation home rental

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This recently renovated and expanded 3 bedroom, 2 bathroom home offers fantastic sea breezes and views of Nantucket Sound. The living room and queen bedroom also have views of the water. The new kitchen is bright and functional with granite countertops and a large sep …see more

from $343 / night

$2,400 / week

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from $343 / night

52

Vacation home in Chatham

Cape Cod / Chatham

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate features the largest private shoreline in Chatham. Watch glorious sunsets while swimming in your infinity edge pool; or cook dinner in the …see more

from $4,000 / night

$28,000 / week

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from $4,000 / night

(1) Very Good 

29

Vacation home in Chatham

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Experience a glimpse of Cape Cod waterfront living at this three-bedroom Chatham home, a dog-friendly property with a wrap-around deck, panoramic views of the ocean and Oyster River, and nearby access to Harding's Beach. This quaint two-level home is scenically situate …see more

from $111 / night

$777 / week

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Responds fast!
avg. 1 hour 41 minutes

from $111 / 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
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

11

Vacation home in Chatham

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Enjoy the Cape from this bright, beautiful townhouse on bustling Main Street in Chatham! This lovely multi-level townhouse is cozy and offers guests two bedrooms and two and a half baths. Two bedrooms, each with one queen sized bed, as well as a double sized sleep sofa …see more

from $186 / night

$1,300 - $1,700 / week

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from $186 / 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
  • Pet friendly
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

26

Vacation home rental

Chatham / North Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
Luxury Chatham Home, Water Views, Private Beach Peak Summer Weekly Rates: $5,150-$5,950 Rents Saturday to Saturday during peak season Linens included The home is set in a private neighborhood with tranquil views of Pleasant Bay and a one minute walk to a private ass …see more

from $357 / night

$2,500 - $5,800 / week

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from $357 / night

18

Home rental in Chatham

Cape Cod / Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rates~~$3225, including the cleaning fee Off Season~~$2725 per week including the cleaning fee Gorgeous, updated rental with tons of open living space. This is a great beach rental, within 1/2 mile to Ridgevale Beach. Terrific family neighborhood spot for ki …see more

from $357 / night

$2,500 - $3,000 / week

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from $357 / night

19

Home rental in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Walk to Main Street in Chatham and enjoy Oyster Pond, which is 2/10 of a mile from this great in town vacation rental home. Enjoy three bedrooms and two full baths on the second level and an open floor plan with living, dining and half bath on the first floor. Walk to t …see more

from $529 / night

$3,700 / week

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from $529 / 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

30

Chatham Vacation home rental

Cape Cod / Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 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 $929 / night

$6,500 - $9,000 / week

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from $929 / 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

$1,600 - $4,495 / week

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Responds fast!
avg. 36 minutes

from $275 / night

12

Vacation home in West Chatham

Chatham / West Chatham

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • 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

from $200 / night

$1,400 / week

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from $200 / night

13

Home rental in Chatham

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Stay in the heart of Chatham Village in this well-maintained 3 bedroom 1.5 bathroom home. Situated in a quiet neighborhood only 4/10ths of a mile from the shops and restaurants on Main Street, baseball field, playground and the Fish Pier. This traditional Cape home fe …see more

from $258 / night

$1,800 / week

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from $258 / night

5

Vacation home in Chatham

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate: $1650 per week, including the cleaning fee~~No Off-Season Updated and light two bedroom home, on Hitching Post Rd near the ball field and the playground! Great yard for kids to play while you enjoy spending time in the sunroom! It is a short walk to th …see more

from $215 / night

$1,500 / week

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from $215 / night

(1) Excellent 

18

Chatham Vacation home rental

Cape Cod / Chatham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Magnificent waterfront home with views of Pleasant Bay, North Beach and the Atlantic beyond. This updated and well-appointed 4 bedroom, 3 1/2 bath home is located in an association neighborhood, water-front home with breathtaking views of Pleasant Bay, North Beach and …see more

from $900 / night

$6,300 / week

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from $900 / night

11

Home rental in Chatham

Cape Cod / Chatham

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rates: IN SEASON: $1800 per week (June 16-Sept 8) ~~Pre-season (May 12-June 16) $1,200 per week ~~Post-season (Sept 8-Oct 12th) $1,200 per week $175 MANDATORY cleaning fee per lease Light and airy - hardwood floors, lots of windows make this beach cottage a …see more

from $172 / night

$1,200 - $1,800 / week

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from $172 / 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

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

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
  • Pet friendly
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

8

Vacation home rental

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
2018 Rental Rate: $2225 per week, including the cleaning fee ~~Off-season: $1525/wk, including cleaning fee Lovely updated cottage located in the popular Harding's Hills neighborhood. Spacious master bedroom with cathedral ceiling and private bath. The kitchen is also u …see more

from $192 / night

$1,350 - $2,050 / week

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from $192 / night