50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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Vacation rentals Cape Cod
3,283 properties
Martha's Vineyard
720 properties
Apartments Nantucket
520 properties
Apartments Boston
254 properties
Vacation rentals Cape Ann
146 properties
Apartments Berkshires
118 properties
Apartments Cambridge
49 properties
Apartments Somerville
27 properties
Apartments Plymouth
26 properties
Waltham
16 properties
Ipswich
16 properties
Hampshire County
13 properties
Brookline
13 properties
Apartments Marshfield
12 properties
Newbury
12 properties
Apartments Scituate
11 properties
Beach rentals Salisbury
10 properties
Apartments Marion
9 properties
Apartments Newburyport
6 properties
Apartments Chelsea
6 properties

Massachusetts

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5,507 Vacation rentals

(6) 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 $185 / night

$995 - $2695 / week

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from $185 / night

24

Vacation windmill rental

Cape Cod / Centerville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Fernbrook Windmill comprises a modern fully-serviced house built in a Classic Cape style around the original windmill that served the Fernbrook Estate. The original windmill was built in 1881 to draw fresh water for the Fernbrook Estate. A 'Cape Style' addition was buil …see more

from $1226 / night

$8576 / week

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Responds fast!
avg. 2 hours 22 minutes

from $1226 / night

(3) Excellent 

24

Vacation apartment rental

Massachusetts / Plymouth

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • 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

$1300 / week

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from $235 / 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

$1600 - $4495 / week

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Responds fast!
avg. 1 hour 41 minutes

from $275 / night

12

Vacation home in Dennis Port

Cape Cod / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
  • Air conditioning
Enjoy your vacation just steps away from a private, family friendly beach on Nantucket Sound. The cottage is located a few houses away from the Oak Street Private Beach. Cottage includes flat screen TV, cable, wi-fi, window AC unit, full kitchen, indoor/outdoor shower, …see more

from $150 / night

$1050 / week

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from $150 / night

14

Vacation home in Massachusetts

Massachusetts / Plum Island

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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

$3150 - $3450 / week

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from $399 / night

(10) 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

$1428 / week

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Responds fast!
avg. 3 hours 31 minutes

from $204 / night

13

Vacation guest house in Vineyard Haven

Martha's Vineyard / Vineyard Haven

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Private garden
This property is in downtown Vineyard Haven within the historic district. The barn has a sleeping loft, open living, dining & kitchen area. The efficiency kitchen has a two burner cooktop,under counter refrigerator,coffee maker,microwave and large capacity convection …see more

from $245 / night

$1715 / week

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Responds fast!
avg. 2 hours 13 minutes

from $245 / night

(19) Excellent 

65

Apartment rental in Boston

Massachusetts / Boston

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
Contemporary One Bedroom, One Bath fully furnished condominium home (711 SF) at a Luxury Condominiums Building at the Boston/Charlestown historic Navy Yard, on the waterfront of Boston Harbor, situated right on the freedom trail and historic attractions such as the USS …see more

from $165 / night

$1050 - $1595 / week

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Responds fast!
avg. 2 hours 18 minutes

from $165 / 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

Pricing unknown

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Pricing unknown

20

Home rental in Orleans

Cape Cod / Orleans

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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 $200 / night

$1400 - $1800 / week

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from $200 / 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 $284 / night

$1988 - $2789 / week

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from $284 / night

39

Vacation home with golf nearby in West Chatham

Chatham / West Chatham

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Suitable for children age 5+
ACCOMMODATIONS: 3 bedrooms plus den with 2.5 baths. Accommodating 8-10 people. Master suite: king bed w/en suite Guest room 1: queen bed Guest room 2: four twin beds (2 bunks) Guest room 3: den w/full bed Living room Dining room seats 8 (addition kitchen table sea …see more

from $415 / night

$2200 / week

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from $415 / night

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

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 $736 / night

$5150 - $5400 / week

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from $736 / 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

$3401 / week

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Responds fast!
avg. 1 hour 22 minutes

from $486 / night

17

Vacation home in Dennis Port

Cape Cod / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.1 mi
  • Child friendly
Enjoy your vacation just steps away from a private, family friendly beach on Nantucket Sound. The cottage is located a few houses away from the Oak Street Private Beach. Cottage includes flat screen TV, cable, wi-fi, window AC unit, full kitchen, indoor/outdoor shower, …see more

from $215 / night

$1500 / week

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from $215 / night

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

$1225 / week

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from $175 / 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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Pricing unknown

6

Vacation apartment in Massachusetts

Massachusetts / Boston

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
This is a test property - do not book or inquire. This is a test property - do not book or inquire. This is a test property - do not book or inquire. This is a test property - do not book or inquire. This is a test property - do not book or inquire. This …see more

from $13 / night

$90 / week

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Responds fast!
avg. 10 minutes

from $13 / night

7

Condo rental in Massachusetts

Massachusetts / Natick

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
Light and contemporary 2 bedrooms, 2 bathrooms condo with everything you need for a comfortable stay. Perfect for a family with up to 4 kids or for 2 couples. Spacious master bedroom, additional bedroom, and bathroom. Both rooms have large closets. Enjoy the pool and te …see more

from $110 / night

$695 - $1115 / week

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from $110 / night

(1) Excellent 

11

Vacation home in Sagamore Beach

Bourne / Sagamore Beach

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Perfect turn-key Sagamore Beach rental home that is a 2-minute walk to the beach. This 4 bedroom home features tons of light, a large finished basement perfect for kids and still holds that "new" home, sparkling clean factor since it was built in 2004. Features a wonde …see more

from $300 / night

$2000 - $2300 / week

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from $300 / night

(3) Very Good 

9

Home rental in Chatham

Cape Cod / Chatham

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden
Beachfront property, close to town and lighthouse. Cottage is in Chatham's Old Village. …see more

from $250 / night

$1500 / week

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from $250 / night

33

Vacation home in Yarmouth Port

Cape Cod / Yarmouth Port

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
New, Spacious, Casually Elegant Home with Privacy and Stunning Views (linens included) Peak weekly rate $3,800 (Rents Saturday - Saturday during peak season) You'll enjoy a lot of house for the money here. Tucked away in a private neighborhood in Yarmouth Port, you'll f …see more

from $350 / night

$2000 - $3500 / week

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from $350 / night

(14) Very Good 

20

Apartment rental in Hyannis

Cape Cod / Hyannis

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This cozy one bedroom, one bath cottage is just steps to Sea Street and Keyes Beach. Cottage features a newly renovated open living room, fully equipped kitchen, dining area and spacious bedroom. AC in the bedroom and living room. Enjoy the lovely water views and breath …see more

from $135 / night

$1265 / week

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from $135 / night

40

Vacation home in Orleans

Cape Cod / Orleans

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Newly remodeled historic home. Heated Pool, Central AC, Sleeps 12, Linens & Towels Included! Peak Summer Weekly Rates: $9,500 (Rents Saturday - Saturday during peak season) This beautiful 1920 Orleans home, newly remodeled and redecorated, exudes Cape Cod charm, retains …see more

from $750 / night

$4000 - $9500 / week

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from $750 / night

(21) Excellent 

13

Vacation cottage rental

Berkshires / Great Barrington

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hi …see more

from $179 / night

$1295 - $1845 / week

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from $179 / night

36

Newburyport Vacation apartment rental

Massachusetts / Newburyport

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
The Space Inside you will find bright pops of color that add a bit of whimsy, as well as a full kitchen, living area, and all the comforts of home. However, with the beach so close, you won't want to spend too much time indoors! Step inside this cozy unit to find a livi …see more

from $129 / night

$851 - $1200 / week

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from $129 / night

25

Home rental in Lanesboro

Berkshires / Lanesboro

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and a …see more

from $195 / night

$1500 - $1750 / week

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from $195 / night

(15) Very Good 

30

West Harwich Vacation home rental

Harwich / West Harwich

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Child friendly
We make your vacation special. From the moment you come through the front door of our upstairs 2 bedroom home with central airconditioning living room with 2 sofa recliners beckons you to relax but the kitchen comes equipped with an electric cook top and wall …see more

from $100 / night

$900 - $1500 / week

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Responds fast!
avg. 3 hours 38 minutes

from $100 / night

26

Vacation home in Brewster

Cape Cod / Brewster

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Waterfront Brewster Cottage with Private Beach PRIME SUMMER WEEKLY RATE:  $4,200 - $4,400 (Rents Saturday to Saturday during peak season) A classic Cape Cod cottage, directly on a perfect sandy, private association beach. There is 450 feet of beach front, with private a …see more

from $315 / night

$2200 - $4400 / week

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from $315 / night

24

Home rental in Dennis Port

Cape Cod / Dennis Port

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
#902 Sea Stars Cottage: Adorable! This updated cottage is centrally located by Nantucket Sound beaches, shopping and restaurants. Sweet little neighborhood lined with quaint beach cottages, perfect area for bike riding and outdoor entertaining. Immediate feeling of CLEA …see more

from $89 / night

$799 - $999 / week

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from $89 / night

(14) Excellent 

15

Vacation home in Massachusetts

Massachusetts / Plymouth

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Suitable for children age 5+
Welcome to Settling Inn. Your private accommodations include a large beautifully and newly furnished in-law apartment with private parking. You'll enter an open living room with a cathedral ceiling, skylights and exposed pine beams. The full kitchen and dining area is d …see more

from $175 / night

$1100 - $1515 / week

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from $175 / night

36

Truro Vacation home rental

Cape Cod / Truro

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
Luxurious Truro Home And Guest House, 3 Private Wooded Acres On Beautiful Great Pond Ideal Couples Retreat Or For Family Gathering Peak Summer Weekly Rates: $6,000-$6,500 Ideally situated on the Outer Cape in South Truro, this magnificently renovated property provides s …see more

from $415 / night

$2900 - $6700 / week

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from $415 / night

25

Vacation home in South Yarmouth

Cape Cod / South Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
4 beds / 2 baths / Outdoor Shower (RANCH) This is truly beautiful summer getaway just .6 miles (5 minute walk) to the beach (e.g. Parker’s River Beach), .5 miles to Skull Island (mini golf-entertainment complex), .5 miles to the Irish Village for your entertainment an …see more

from $100 / night

$2520 / week

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from $100 / night

(15) Very Good 

15

Hyannis Vacation home rental

Cape Cod / Hyannis

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
This wonderful 3 bedroom, one and a half bath home is fully equipped with all the necessities and an enclosed outdoor shower. The 3 bedrooms are upstairs with a full bath with a jet tub, and they include a master bedroom with a queen bed and 2 more bedrooms with twin be …see more

from $250 / night

$1400 - $1950 / week

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from $250 / night

9

Teaticket Vacation condo rental

Falmouth / Teaticket

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
Mariners Point Ocean front Resort in a luxury, prime location on Vineyard Sound; minute to Island Queen Ferry to Martha's Vineyard. Condo is fully equipped to accommodate 4. I am renting 4 summer mid July/Aug. calendar weeks 28,29, 32,33. and 1 mid Sept. wk 37. 7 night …see more

from $165 / night

$1150 / week

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from $165 / night

(1) Excellent 

14

Vacation cottage rental

Cape Cod / Wellfleet

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Nestled within the tranquil pines, this desirable vacation spot is centrally located within the National Seashore with easy access to all of Wellfleet's ocean & bay beaches, fresh water ponds and the bike trail. Part of the prestigious 'Deck 2' complex, this contempo …see more

from $125 / night

$650 - $1250 / week

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from $125 / night

24

Home rental in Wellfleet

Cape Cod / Wellfleet

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
#309 Victorian Dream:  Originally built in (****) , though it's been completely restored to date with the modern conveniences and luxury that we strive to offer our guests in every home. Peeks of harbor! Renovated, eat-in kitchen with custom cabinetry and soap stone cou …see more

from $149 / night

$999 - $1699 / week

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from $149 / night

16

Vacation home in Centerville

Cape Cod / Centerville

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary
3 bedroom, 2 bath upscale home in cul de sac neighborhood in perfect location - close to beaches, bike paths, town and shopping. The home has a large, updated kitchen with breakfast bar, separate dining area and sliders out to the deck. Amenities include: washer & drye …see more

from $180 / night

$1250 - $1500 / week

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Responds fast!
avg. 2 hours 14 minutes

from $180 / night

1