50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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Vacation rentals Cape Cod
3,174 properties
Apartments Nantucket
1,166 properties
Martha's Vineyard
826 properties
Apartments Boston
507 properties
Brookline
149 properties
Vacation rentals Cape Ann
136 properties
Apartments Berkshires
130 properties
Apartments Cambridge
59 properties
Apartments Plymouth
26 properties
Apartments Somerville
25 properties
Apartments Scituate
16 properties
Ipswich
14 properties
Hampshire County
14 properties
Apartments Marshfield
10 properties
Apartments Salem
7 properties
Apartments Marblehead
7 properties
Apartments Wareham
7 properties
Beach rentals Salisbury
7 properties
Brimfield
6 properties
Apartments Newburyport
6 properties

Massachusetts

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6,135 Vacation rentals

23

Vacation home in Massachusetts

Massachusetts / Plum Island

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Coveted Oceanfront at the Entrance of the Merrimac River. Enjoy 3 levels of decks as you watch the boats pass thru the Breakers. Enjoy panoramic views from the rooftop deck from the coastline of Maine & New Hampshire North to the Isles of Shoal East to Rockport & Glouce …see more

from $399 / night

$3,150 / week

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from $399 / night

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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avg. 1 hour 22 minutes

from $275 / night

(3) Excellent 

24

Vacation apartment rental

Massachusetts / Plymouth

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
A beautiful one-bedroom with additional queen sleep-sofa in the heart of historic Plymouth harbor is waiting for you. Not more than 15 yards to the water and a 3-minute walk to the Mayflower and Plymouth Rock, this location couldn't be better for a vacation rental in P …see more

from $235 / night

$1,300 / week

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avg. 2 hours 5 minutes

from $235 / night

31

Vacation home with golf nearby in Stockbridge

Berkshires / Stockbridge

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
THE ESCAPE at Stockbridge. Enjoy our Open & Spacious Newly built house in the Berkshires, Complete Privacy! No Visible Neighbors. -1 1/2 miles to downtown Stockbridge, -just minutes to Norman Rockwell museum, Chesterwood, Naumkeag, Tanglewood & Kripalu. -Housatonic R …see more

from $250 / night

$1,950 - $3,150 / week

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from $250 / night

(9) Very Good 

24

Vacation cottage with golf nearby in New Seabury

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly
Lovely open-plan home furnished in comfortable, casual style. Fully-equipped kitchen with counter seating, dining area and sitting area with TV, flow into second step-down sitting area which opens with sliding glass doors onto deck and back yard. Master bedroom (with …see more

from $250 / night

$1,500 - $2,750 / week

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from $250 / night

20

Massachusetts Vacation home rental

Massachusetts / Nantucket

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
This classic and historic Nantucket sea captain's house (part of Nantucket's Historic Registry) was built in 1807 is located on Nantucket Island lying east of Cape Cod, Massachusetts, easily accessible from Boston. Carefully restored by its owners, the home is a short …see more

from $772 / night

$5,400 / week

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from $772 / night

18

Home rental in Massachusetts

Massachusetts / Marblehead

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Home originally built in 1923. Purchased and completely renovated in 2004. 1600 sq. ft. As you step onto a mahogany front porch, you open a walnut wood front door into a spacious open floor plan. Diningroom, livingroom and kitchen are bright and cheerful. First floor …see more

from $320 / night

$2,240 - $2,275 / week

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from $320 / night

4

Home rental in Somerville

Massachusetts / Somerville

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
Our 3 bed, 2 bath, townhouse is business ready with wifi, 50inch tv with full cable, keurig & coffee/tea and flexible check-ins. We have a stock of DVDs, blowdryer, iron, universal charging station, a collection of frequent forgettables from all our travels, and hand w …see more

from $250 / night

$1,750 / week

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from $250 / night

(12) Very Good 

19

Vacation home in Eastham

Cape Cod / Eastham

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Cosy, welcoming home in South Eastham on the outer Cape. The property is well equipped and with lots of space for families or groups. Our traditional Cape Cod house features 4 bedrooms, 2 baths, a generous open plan living/dining/kitchen leading out to a deck. The hous …see more

from $204 / night

$1,428 / week

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avg. 3 hours 39 minutes

from $204 / night

20

Home rental in Orleans

Cape Cod / Orleans

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
Our home is located in a quiet upscale neighbourhood close to all amenities. Walk to grocery store, downtown shopping, library, tennis courts and town field. Less than a 5 minute drive to ocean and bay. Quick access to highway and all the surrounding Cape towns. Rel …see more

from $250 / night

$1,800 / week

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from $250 / night

13

Cottage rental in Dennis Port

Dennis / Dennis Port

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to Stone's Throw, just steps from the warm waters of Nantucket Sound! Under new ownership for the 2018 season! Two bedroom, one bathroom rental unit at the Stone's Throw property. Just a "Stone's Throw" to popular Sea Street Beach on Nantucket Sound. Also enjoy …see more

from $240 / night

$1,500 / week

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from $240 / night

52

Vacation home in Centerville

Cape Cod / Centerville

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Close your eyes and imagine the perfect beach house .Well that's what Mc's Shack Beach House . Situated down a leafy lane right on the beach, on your own private stretch of beach. Mc's Shack Beach House is approx 1700 sq ft ,it has 2 large bedrooms ,a large livingro …see more

from $374 / night

$2,618 - $2,975 / week

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from $374 / night

4

Apartment rental in Massachusetts

Massachusetts / Cambridge

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
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from $10 / night

$70 / week

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from $10 / night

14

Provincetown Vacation condo rental

Cape Cod / Provincetown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
A rare historic gem located in Provincetown's Gallery District at the top of Pearl St. This exclusive unit is one of two redeveloped from a 19th-century barn that later served as the Cape School of Art and the studio and residence of the American painter Edwin Dickinson …see more

from $486 / night

$3,400 / week

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avg. 3 hours 3 minutes

from $486 / night

9

Vacation home in Teaticket

Falmouth / Teaticket

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Our home offers 5 bedrooms, 3 full baths, spacious full kitchen and dining area, washer and dryer, family room with TV,  WIFI, outdoor gas grill, heated pool, space to lounge, sandy area with fire pit and hammock under the trees.     Create lasting memories in our compl …see more

from $300 / night

$2,100 - $3,500 / week

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from $300 / night

19

B&b rental in Massachusetts

Nantucket / Siasconset

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
Sea Lion is a 4 bedroom house located in the heart of Tom Nevers. In the summer it's a holiday rental house, in the winter I transform it into a Bed & Breakfast, and live on-site as your hostess. Space Sea Lion is a classic Tom Nevers Upside Down House with 4 decks and …see more

from $250 / night

$1,750 / week

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avg. 57 minutes

from $250 / night

(1) Good 

6

Vacation apartment in Massachusetts

Massachusetts / Boston

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Air conditioning
Large, bright apartment located steps from Coolidge Corner. 1 bed/1 bath. Fully equipped kitchen with dishwasher. There is also a gym and laundry located in the building. Across the street from a T stop and walking distance to the heart of Coolidge Corner. …see more

Pricing unknown

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17

Apartment rental in Orleans

Cape Cod / Orleans

2 4 6 nights min

  • 2 bedrooms
  • Sleeps 4
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
2 bedroom 1 bath apartment with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Queen bed in one room and a double bed in the other room. Optional air mattress can be set up in living room to sleep 2 more if needed. Window AC units in b …see more

from $175 / night

$1,225 / week

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from $175 / night

6

Vacation home in Massachusetts

Massachusetts / Boston

3 4 Min stay varies

  • 3 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Quiet but just a minute off the interstate, a great place to stay for a few days. Easy access to Newton, Cambridge or Boston. Lovely deck and backyard to relax in the summer. 3 bedrooms and a playroom spread over 3 floors, a garage. A BBQ and a backyard make your stay v …see more

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29

Home rental in Massachusetts

Nantucket / Siasconset

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Nantucket is a magical little island located 30 miles off the shores of Cape Cod. It's steeped in the history of its whaling founding fathers. Grey shingled houses dot the coastline, the streets in town are paved in cobblestones, and the harbor is filled with boats well …see more

from $700 / night

$4,900 / week

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avg. 57 minutes

from $700 / night

6

Massachusetts Vacation townhouse rental

Martha's Vineyard / Edgartown

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Pet friendly
The K-4 Duplex is part of the Winnetu Oceanside Resort - the only Resort at South Beach. It's a 10-minute walk to the beach and is situated at the bicycling/jogging path leading to charming Edgartown. This 'Silver Level' home offers three bedrooms, two-and-a-half bathro …see more

from $883 / night

$6,175 / week

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from $883 / night

5

Vacation home rental

Martha's Vineyard / Oak Bluffs

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 1 mi
  • Child friendly
Nestled in Historical Oak Bluffs is our one level cottage. It features a large (15x37) deck. Location. location. 1.5 miles from either ferry. Oak Bluffs or Vineyard Haven. . Distance to shopping , either town or going to the beach less then 2 miles. Public transportatio …see more

from $300 / night

$2,500 - $2,600 / week

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avg. 3 hours 29 minutes

from $300 / night

4

Vacation apartment in Massachusetts

Massachusetts / Boston

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Great one bedroom apartment with lots of living space and large full bathroom. Complete kitchen including dishwasher and microwave. Free internet and cable access. 24 doorman and paid parking available in lower garage. Many nearby restaurants, bars and a Walgreens. Also …see more

from $1,228 / night

$6,141 / week

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from $1,228 / night

4

Vacation home in Boston

Massachusetts / Boston

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
Beautiful one bedroom penthouse apartment with small balcony overlooking Boston harbor and airport. Walk-able to all major tourist destinations including Fanueil Hall and Quincy market. Many nearby restaurants and bars. Right next to the blue and orange line T stops. Do …see more

from $1,400 / night

$7,000 / week

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from $1,400 / night

26

Apartment rental in Hancock with shared pool

Berkshires / Hancock

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Let this quaint 2-bedroom, 2-bathroom Hancock condo, which sleeps 6, be the perfect destination for your New England escape! Nestled along the scenic border of New York and Massachusetts in the middle of Jiminy Peak Mountain Resort, this pristine Hancock vacation rental …see more

from $185 / night

$1,295 - $2,793 / week

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avg. 8 minutes

from $185 / night

24

West Stockbridge Vacation home rental

Berkshires / West Stockbridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provi …see more

from $165 / night

$1,155 - $1,505 / week

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avg. 1 hour 0 minutes

from $165 / night

(1) Excellent 

10

Hancock Vacation hotel apartment rental

Berkshires / Hancock

2 8 2 nights min

  • 2 bedrooms
  • Sleeps 8
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Lodging at the highest rated resort at Jiminy Peak Mountain--Wyndham Bently Brook Resort-Mountainside What is Jiminy Peak Known For---The Best Skiing in the Berkshire Mountains tucked away in Hancock, Ma. 2 Bedroom Unit consisting of-King bed master, 2 doubles 2nd bedro …see more

from $455 / night

$3,185 / week

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from $455 / night

(1) Excellent 

6

Vacation bungalow in Marshfield

Massachusetts / Marshfield

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
UPDATED 02/02/2018: I have just one week available for Summer 2018; June 23. You can book the entire week OR take your choice of one of two half-weeks. HALF WEEK #1 - ARRIVE SATURDAY 6/23 at 8 A.M. DEPART TUESDAY 6/26 at 7 P.M. HALF WEEK #2 - ARRIVE WEDNESDAY 6/27 a …see more

from $200 / night

$1,250 / week

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from $200 / night

(2) Excellent 

30

Vacation home rental

Berkshires / Stockbridge

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Elevate your Stockbridge experience by staying at this 3-bedroom, 1.5-bath vacation rental house, which sleeps 6 and boasts a private deck. Nestled within the serene forests of the Berkshires, ‘The Redway House’ is the quintessential setting for your next Massachusetts …see more

from $215 / night

$1,505 - $2,485 / week

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avg. 7 minutes

from $215 / night

35

Vacation home in Vineyard Haven

Martha's Vineyard / Vineyard Haven

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Relax and enjoy the picturesque views of the outer harbor, with its plethora of boats going by each day, from the screened Gazebo, porch and patio areas. The wide, sandy private beach offers excellent swimming for both adults and children. The large yard with beautiful …see more

from $572 / night

$4,000 - $8,550 / week

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from $572 / night

35

Provincetown Vacation home rental

Cape Cod / Provincetown

4 8 Min stay varies

  • 4 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 $284 / night

$2,025 - $4,499 / week

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from $284 / night

(12) Excellent 

16

Cottage rental in Eastham with shared pool

Cape Cod / Eastham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
This 3 bedroom, 2 bathroom Cape Cod cottage is located on a pond. About 1 1/2 miles from the National Sea Shore and Cape Cod Bay as well. Two bedrooms have full size beds and one bedroom has two twin beds. The cottage comfortably sleeps 6. We rent by the night o …see more

from $100 / night

$700 - $1,000 / week

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from $100 / night

(1) Excellent 

11

Apartment accommodation in Massachusetts

Massachusetts / Upton

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
Private studio apt with separate entrance. King-size bed plus sofa bed allows for four guests. Extra large bathroom with soaking tub. Complete kitchen. Outdoor deck overlooking the woods with great hiking trails. Great executive stay option. Babysitter available on …see more

from $75 / night

$475 - $545 / week

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avg. 2 hours 14 minutes

from $75 / night

5

Vacation condo with shared pool in Dennis Port

Dennis / Dennis Port

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
The Breakers Resort is situated beachfront and center, just waiting for your next vacation. This cozy, beachside community is the ultimate home-away-from-home in ever-popular Cape Cod. The Breakers offers visitors every opportunity to relax and recharge, whether on the …see more

from $215 / night

$1,300 / week

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from $215 / night

40

Home rental in Gloucester

Cape Ann / Gloucester

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Ask about children
Imagine a summer of bliss, swimming from the dock at high tide, or from the sandy beach at low tide, when you stay at Annisquam Singing Pines. Or easily paddle to one of the nearby islands or to Wingaersheek Beach for a day in the sand and surf. Annisquam Singing Pin …see more

from $670 / night

$3,530 - $4,380 / week

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from $670 / night

(30) Excellent 

Certificate of Excellence

30

Vacation condo in Hyannis

Cape Cod / Hyannis

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Great location for walking the beach, dining, shopping or just relaxing! Walk to Sea St. Beach and Keyes beach which is only 150 feet from your door. This two bedroom cottage can sleep 6 and is the perfect vacation spot. All Bed and Bath Linens are included. Enjoy the l …see more

Certificate of Excellence

from $175 / night

$1,400 - $1,895 / week

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avg. 1 hour 32 minutes

from $175 / night

18

Apartment rental in Brewster with shared pool

Cape Cod / Brewster

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
C-Style, Renovated, Golf View. Close to Pool, 2 ACs, 4 Pool Passes (Fees Apply) Ready to Rent for the 2018 Season! Golf Course View and located close to the Fletcher pools, tennis & basketball courts, this desirable Trevor Village townhouse features renovated bathr …see more

from $158 / night

$1,105 - $2,005 / week

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from $158 / night

(7) Very Good 

9

East Sandwich Vacation cottage accommodation

Sandwich / East Sandwich

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Adorable waterfront unit of a three unit property located right on East Sandwich beach. Enjoy the great view of beautiful Cape Cod Bay. Waterfront patio, outside shower and huge sandbar makes this a perfect vacation spot. Bright and white. Cable television and DVD playe …see more

from $133 / night

$925 - $1,875 / week

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from $133 / night

24

Vacation home rental

Cape Cod / Eastham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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 $104 / night

$729 - $1,799 / week

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from $104 / night

18

Vacation home in Falmouth

Cape Cod / Falmouth

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Perfectly situated along the bank of one of the Cape's most beautiful (and active) harbors, The Captain's Quarters is really two homes for the price of one! The main house is a traditional Cape with all everything on one floor including a full kitchen, dining space (wit …see more

from $321 / night

$2,250 / week

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avg. 3 hours 16 minutes

from $321 / night