50 Best Massachusetts Apartments on Holiday Lettings - Vacation rentals

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Vacation rentals Cape Cod
3,269 properties
Martha's Vineyard
771 properties
Apartments Nantucket
519 properties
Apartments Boston
260 properties
Vacation rentals Cape Ann
140 properties
Apartments Berkshires
113 properties
Apartments Cambridge
49 properties
Apartments Somerville
27 properties
Apartments Plymouth
26 properties
Ipswich
17 properties
Waltham
16 properties
Apartments Marshfield
14 properties
Brookline
13 properties
Newbury
12 properties
Apartments Newburyport
8 properties
Hampshire County
8 properties
Apartments Quincy
8 properties
Apartments Scituate
8 properties
Apartments Newton
7 properties
Apartments Salem
6 properties

Massachusetts

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5,572 Vacation rentals

(11) Excellent 

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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from $1226 / night

(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 $150 / night

$1295 - $2695 / week

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from $150 / 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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from $275 / 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

(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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from $204 / 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

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 - $2788 / week

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from $284 / night

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

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

(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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from $165 / 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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from $245 / 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

4

Massachusetts / East Longmeadow

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly

from $5424 / night

$37967 / week

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from $5424 / 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

$3400 / week

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from $486 / night

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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from $13 / 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

(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

19

Apartment rental in Orleans

Cape Cod / Orleans

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
2 bedroom 1 bath dwelling with separate private entrance, driveway and deck. Living room, kitchen, and laundry. Bunk bed with double bed on the bottom and single on the top in one room and a double bed in the other room. Optional air mattress can be set up in living ro …see more

from $175 / night

$1225 / week

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from $175 / night

(5) Excellent 

21

Massachusetts / Nantucket

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 4 mi
  • Child friendly
  • Car not necessary

from $800 / night

$5600 / week

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from $800 / night

13

Martha's Vineyard / Edgartown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children

from $171 / night

$1200 - $2800 / week

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from $171 / night

17

Martha's Vineyard / Oak Bluffs

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Air conditioning

from $429 / night

$3000 - $3900 / week

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from $429 / night

(3) Very Good 

9

Cape Cod / Chatham

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Air conditioning
  • Private garden

from $250 / night

$1500 / week

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from $250 / night

(12) Excellent 

60

Cape Cod / West Hyannisport

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Child friendly

from $230 / night

$1100 - $1600 / week

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from $230 / night

(2) Excellent 

16

Cape Cod / Dennis

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $150 / night

$700 - $1400 / week

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from $150 / night

(3) Excellent 

22

Martha's Vineyard / Oak Bluffs

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning

from $250 / night

$1250 - $2000 / week

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from $250 / night

15

Martha's Vineyard / Edgartown

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Air conditioning

from $571 / night

$4000 - $10000 / week

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from $571 / night

8

Bourne / Sagamore Beach

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly

from $125 / night

$800 - $1000 / week

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from $125 / night

25

Berkshires / Lanesboro

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

from $195 / night

$1500 - $1750 / week

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from $195 / night

43

Cape Cod / Barnstable

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden

from $399 / night

$2975 / week

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from $399 / night

24

Cape Cod / Mashpee

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Air conditioning

from $299 / night

$2093 / week

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from $299 / night

12

Berkshires / Lenox

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from $225 / night

$1415 / week

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from $225 / night

(3) Excellent 

17

Harwich / Harwich Port

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly

from $300 / night

$1800 - $5100 / week

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from $300 / night

18

Cape Cod / Dennis Port

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

from $150 / night

$700 - $1400 / week

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from $150 / night

(8) Excellent 

13

Cape Cod / South Dennis

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden

from $150 / night

$750 - $1100 / week

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from $150 / night

36

Chatham / North Chatham

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

from $500 / night

$3500 - $5500 / week

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from $500 / night

(8) Very Good 

6

Cape Cod / Hyannis

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets

from $95 / night

$665 - $850 / week

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from $95 / night

11

Berkshires / Hinsdale

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from $140 / night

$800 - $920 / week

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from $140 / night

(21) Very Good 

47

Massachusetts / Plymouth

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

from $135 / night

$875 - $1020 / week

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from $135 / night

(13) Excellent 

16

Cape Cod / Truro

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $165 / night

$650 - $1425 / week

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from $165 / night

(5) Excellent 

32

Berkshires / Stockbridge

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

from $499 / night

$2499 - $3805 / week

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from $499 / night

1