50 Best Chatham Vacation rentals on Holiday Lettings - Apartments

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South Chatham
43 properties
North Chatham
28 properties
West Chatham
8 properties

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2,592 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

(2) Very Good 

34

Vacation home in Chatham

Cape Cod / Chatham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
Central Air and Dog Friendly! Totally Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Large family? No problem! Can't leave home without Fido? Bring your doggie along! Everything is here to for you and your group to hav …see more

from $425 / night

$2,100 - $4,500 / week

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from $425 / night

20

Vacation home in Chatham

Cape Cod / Chatham

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $4,725 including cleaning fee FRIDAY TO FRIDAY Rental ~~ Off Season: $3,725 including the cleaning fee Beautiful, new home centrally located in Chatham with upscale and lavish furnishings throughout. Simple elegance defines the home with Custom Hardwoo …see more

from $500 / night

$3,500 - $4,500 / week

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from $500 / night

(3) Excellent 

18

Home rental in Chatham

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Spend your Cape Cod vacation sunbathing by the pool at this 3 bedroom, 2.5 bath Chatham vacation rental home. This home is located at the end of a cul-de-sac just 3/10ths of a mile from Pleasant Street Beach and Forest Beach on Nantucket Sound. The pool is surrounded …see more

from $429 / night

$3,000 / week

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from $429 / 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

40

Chatham Vacation home rental

Cape Cod / Chatham

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
Waterfront views of Bucks Creek.  Pet Friendly! 3 Bedroom and 2 Baths-sleeps 8. Slimline AC units to keep you cool and WiFi to keep you connected. Walk to Ridgevale Beach! Enter the front door to a hallway.  To the left is an eat-in fully equipped kitchen with double s …see more

from $314 / night

$2,200 - $3,700 / week

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from $314 / 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

10

Chatham Vacation condo rental

Cape Cod / Chatham

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • 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 $358 / night

$2,500 / week

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from $358 / 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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Responds fast!
avg. 3 hours 46 minutes

from $450 / night

12

Vacation condo in Chatham

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Lovely, renovated and very clean. Two-full bath condo near Ridgevale Beach. No roads to cross to access the beach road. Full kitchen and dining; Enjoy the private patio area with weber grille overlooking lovely plantings and lawn area. air conditioning , comfortable f …see more

from $243 / night

$1,700 / week

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Responds fast!
avg. 1 hour 13 minutes

from $243 / night

15

Vacation home rental

Cape Cod / Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Walk to Pleasant Street Beach, Renovated, Central AC, King Bed This newly remodeled, bright and beautifully decorated, 3 bedroom, 3 bath home is a short stroll to 2 of Chatham's Nantucket Sound beaches: Pleasant Street Beach (3/10's mile) and Forest Beach (4/10's mil …see more

from $542 / night

$3,790 / week

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from $542 / night

24

Vacation home in North Chatham

Chatham / North Chatham

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Come stay at: Misty Meadow! Enjoy this lovely condo with all amenities including Central AC mini split and free WiFi Conveniently located too. Situated in a very quiet area of North Chatham offering private conservation views from this charming one bedroom, first floo …see more

from $121 / night

$850 - $1,275 / week

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from $121 / night

19

Vacation home rental

Chatham / North Chatham

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
105 Fox Hill Road (#133951) - Beautiful Home with Fairway Views! Beautiful Home with Fairway Views of Eastward Ho! This lovely home masterfully combines the charm and grace of an antique with the updates and amenities of a newer home. Set on a parcel of land overlookin …see more

from $418 / night

$2,925 / week

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from $418 / night

36

Chatham Vacation home rental

Cape Cod / Chatham

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. Imagine walking through the front door to a stunning view of the water overlooking Chatham pier and your own heated pool. Relax in the hot tub or sit on the back patio and take it all in. This waterfront vacation hom …see more

from $1,785 / night

$12,500 - $15,000 / week

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from $1,785 / night

(1) Excellent 

22

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 views of Bassing Harbor, Ryder's Cove and Pleasant Bay from this 4-bedroom, 3 bathroom waterfront home perched high on a bluff. This home boasts an expansive deck with plenty of outdoor seating for relaxing or dining alfresco and a spacious yard including a …see more

from $600 / night

$4,200 / week

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from $600 / night

14

Vacation home in Chatham

Cape Cod / Chatham

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ask about children
  • Air conditioning
2018 Rental Rate: $3675 per week including the cleaning fee ~~ Off-Season: $2675 per week including the cleaning fee Clean & comfortable 3-bedroom ranch with central air, located in the private neighborhood of Harding's Shores. Walk to your own private stretch of sand f …see more

from $357 / night

$2,500 - $3,500 / week

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from $357 / 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 bed …see more

from $385 / night

$2,700 - $5,500 / week

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from $385 / 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

25

Vacation home in Chatham

Cape Cod / Chatham

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • 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 $165 / night

$1,155 - $2,850 / week

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from $165 / night

25

Chatham Vacation home rental

Cape Cod / Chatham

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
11 JEANETTE DRIVE Just over a mile to downtown Chatham and also close to Hardings Beach and Oyster Pond! This great house is convenient to the bike trail, tennis courts and has deeded rights to a fresh water pond! With four bedrooms and two full baths, this updated h …see more

from $372 / night

$2,600 / week

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from $372 / night

18

Vacation home in Chatham

Cape Cod / Chatham

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with t …see more

from $400 / night

$2,800 / week

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from $400 / night

18

Home rental in Chatham

Cape Cod / Chatham

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Waterfront cottage on Nantucket Sound. Enjoy the spectacular location and panoramic waterviews from this 6 bedroom, 2 bath Chatham rental cottage situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few cottages where you can step out your door a …see more

from $672 / night

$4,700 / week

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from $672 / night

36

Vacation home in Chatham

Cape Cod / Chatham

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Experience: Chatham Breeze. 4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. BONUS: Linens included IN SUMMER SEASON. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump a …see more

from $650 / night

$4,500 - $6,400 / week

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from $650 / night

9

Chatham Vacation home rental

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Gorgeous views of Nantucket Sound, Ridgevale Beach and Bucks Creek from this charming 2 bedroom, 1 bath authentic Cape cottage. Located just steps to popular Ridgevale Beach, the only public beach with watersports rentals and a snack bar, this cottage has one bedroom w …see more

from $172 / night

$1,200 / week

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from $172 / night

(1) Excellent 

16

Vacation cottage in Chatham

Cape Cod / Chatham

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Pet friendly
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 to this 3 bedroom/1 bath cottage just down the road from Forest Beach in Chatham. Maybe it's the storybook shu …see more

from $211 / night

$1,475 - $1,712 / week

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Responds fast!
avg. 3 hours 29 minutes

from $211 / night

17

Vacation home rental

Cape Cod / Chatham

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
Enjoy views of Nantucket Sound from every floor of this recently updated, meticulously maintained, 3 bedroom, 2 bathroom Chatham rental property. It is a perfect balance between having all of the modern amenities, with an open, light and bright feel while still maintai …see more

from $415 / night

$2,900 / week

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from $415 / night

20

Chatham Vacation home rental

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
105 Wood Carver Knoll, Chatham - ID# 106342. Spectacular waterfront home in Chatham overlooking Oyster Pond! Central Air, Wireless Internet, gourmet kitchen with espresso machine, Keurig and more. Enjoy the deck with incredible views of Oyster Pond, the church steeples …see more

from $500 / night

$3,500 / week

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from $500 / night

40

Vacation home rental

Cape Cod / Chatham

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Pet friendly
Welcome to Heron Hill! Pet Friendly! This lovely 4 bedroom, 2.5 bath Chatham vacation home overlooks Nantucket Sound and Buck's Creek. Within walking distance to Harding's Beach and just one block to the community dock area which offers easy access for kayaks and canoes …see more

from $400 / night

$2,800 - $4,200 / week

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from $400 / 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

(2) Very Good 

19

Vacation home in Chatham

Cape Cod / Chatham

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Enjoy your Cape Cod vacation in this tastefully decorated, comfortable home. It is located in Hardings Beach Hills, only 4/10ths of a mile from popular Harding's Beach. This 3 bedroom, 2.5 bathroom home has an updated kitchen with granite countertops and stainless ste …see more

from $372 / night

$2,600 / week

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from $372 / night

24

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 recently renovated 3 bedroom, 3 bath home is situated on a nicely landscaped lot nestled at the end of a private road just .2 miles from Pleasant Street Beach. This property has high-quality finishes and décor and a unique layout perfect for extended or multi-gen …see more

from $443 / night

$3,100 / week

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from $443 / night

24

Chatham Vacation home rental

Cape Cod / Chatham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $300 / night

$1,800 - $2,195 / week

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from $300 / night

21

Vacation home in Chatham

Cape Cod / Chatham

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
“Wonderful week! We had a family wedding here in Chatham, so some of our family stayed here. A very cozy cottage in the vintage Cape style! And the weather was spectacular! Bucks Creek area very delightful for walks, beautiful beach and boats at the snack bar! Thanks!” …see more

from $230 / night

$1,607 - $2,081 / week

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Responds fast!
avg. 3 hours 29 minutes

from $230 / night

12

Vacation home in Chatham

Cape Cod / Chatham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
2018 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL Off-Season: $1250 per week including the cleaning fee Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and sitting area with sofa …see more

from $157 / night

$1,100 - $1,800 / week

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from $157 / 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

14

Vacation home in Chatham

Cape Cod / Chatham

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
$3,700/week Peak Season (June 30- September 1) $2,100/week for the weeks of (6/23 and 9/1) $1,800/week Shoulder Season (6/16 and 9/8) $1,600/week Shoulder Season (6/9 and 9/15) $1,400/week (before 6/8 and after 9/22) This light, bright 2 bedroom, 2 bath Chath …see more

from $529 / night

$3,700 / week

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from $529 / night

11

Vacation home in Chatham

Cape Cod / Chatham

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
This traditional Cape Cod beach cottage is just up the hill from Pleasant Street Beach. Cute coastal décor fill the two bedrooms, one with a queen and one with two twins, as well as the living, dining and kitchen area. Amenities include a window AC unit in the living …see more

from $215 / night

$1,500 / week

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from $215 / 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 - $5,250 / week

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Responds fast!
avg. 34 minutes

from $275 / 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 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