Cycling holiday villas and apartments Massachusetts | Holiday Lettings

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • United States
  • Massachusetts
  • All locations
  • Acushnet (1)
  • Ashburnham (1)
  • Belmont (1)
  • Berkshires (17)
  • Boston (11)
  • Brimfield (1)
  • Cambridge (2)
  • Cape Ann (6)
  • Cape Cod (137)
  • Colrain (1)
  • Hampshire County (1)
  • Hull (1)
  • Martha's Vineyard (13)
  • Nantucket (5)
  • New Salem (1)
  • Newburyport (1)
  • Newton (1)
  • Plum Island (1)
  • Plymouth (2)
  • Rockport (1)
  • Salem (1)
  • Salisbury (1)
  • Scituate (2)
  • Seekonk (2)
  • Shelburne Falls (1)
  • Southbridge (1)

More

Less

Also consider

Holiday rentals Cape Cod
2,720 properties
Holiday rentals Martha's Vineyard
775 properties
Apartments Boston
604 properties
Houses Nantucket
501 properties
Apartments Cape Ann
137 properties
Cambridge
114 properties
Berkshires
102 properties
Quincy
52 properties
Somerville
29 properties
Plymouth
24 properties
Houses Worcester
19 properties
Newton
17 properties
Lexington
16 properties
Brookline
14 properties
Estates Waltham
14 properties
Houses Ipswich
13 properties
Scituate
13 properties
Houses Marshfield
12 properties
Houses Newbury
8 properties
Beach rentals Marblehead
8 properties
Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

213 Holiday homes

Filters applied: Cycling holidays (213)

(10) Excellent 

1 / 24

Fernbrook Windmill, Cape Cod - Centerville windmill sleeps 12

Cape Cod / Centerville

6 12 7 nights min stay

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; 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' additio  …see more

from £1165 / night

£8150 - £11650 / week

Book Book View

from £1165 / night

(3) Excellent 

1 / 24

Plymouth Harbor View - Plymouth apartment sleeps 4

Massachusetts / Plymouth

1 4 3 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; 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  …see more

from £134 / night

£688 - £955 / week

Book Book View

from £134 / night

(6) Very Good 

1 / 24

CapeCod-New Seabury-1/2mi Poppy/Spit Beach-Pets OK - New Seabury cottage sleeps 8

Cape Cod / New Seabury

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; 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 £126 / night

£760 - £1447 / week

Book Book View

from £126 / night

1 / 39

On the Water, Cape Cod Chatham, VIEWS, sleeps 10 - West Chatham house sleeps 10

Chatham / West Chatham

4 10 3 nights min stay

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 4 km; 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 £317 / night

£1680 - £2214 / week

Book Book View

from £317 / night

1 / 6

McCormick Cottages - 2 Bedroom rental near beach - South Yarmouth house sleeps 5

Cape Cod / South Yarmouth

2 5 7 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
The cottage available for weekly rentals, Saturday to Saturday. It is a part of a spacious landscaped compound made up of six free standing buildings. Unit has kitchen equipped with a refrigerator, coffee maker, toaster, microwave, dishes, silverware, pots and pans.  …see more

from £134 / night

£878 / week

Book Book View

from £134 / night

(17) Excellent 

1 / 65

Boston Waterfront Luxury Home - Boston apartment sleeps 2

Massachusetts / Boston

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: 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 £149 / night

£989 - £1210 / week

Book Book View

from £149 / night

1 / 15

Massachusetts / Colrain

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Ask owner if suitable for children; Ask about pets; Private garden;
 …see more

from £96 / night

£401 / week

Book Book View

from £96 / night

(5) Excellent 

1 / 23

Gem of South Yarmouth - South Yarmouth house sleeps 8

Cape Cod / South Yarmouth

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Child friendly ;
Newly renovated, spacious vacation home in South Yarmouth - minutes from a great beach, shopping and attractions! Our large, sunlit, well equipped vacation home is ready for your arrival - the house is full of amenities and is suitable for either families or couples vac  …see more

from £146 / night

£840 - £2443 / week

Book Book View

from £146 / night

1 / 14

Luxurious Provincetown Retreat - Provincetown condo sleeps 4

Cape Cod / Provincetown

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Not suitable for children; Air conditioning;
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 £360 / night

£2520 / week

Book Book View

from £360 / night

(2) Very Good 

1 / 19

Beach House w/Water View! - South Yarmouth house sleeps 10

Cape Cod / South Yarmouth

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.3 km; Child friendly ;
Our Beach House is located on a quiet street abutting acres of conservation area, within a 2 minute leisurely walk to several beautiful Nantucket Sound beaches. Magnificent views of salt water march and pond from family room, dining room, kitchen, living room, master be  …see more

from £230 / night

£1222 - £3436 / week

Book Book View

from £230 / night

1 / 52

MC's SHACK BEACH HOUSE - Centerville house sleeps 6

Cape Cod / Centerville

2 6 7 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; 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 £217 / night

£1518 - £1900 / week

Enquire Enquire View

from £217 / night

(1) Excellent 

1 / 20

Massachusetts / Belmont

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; No pets allowed;
 …see more

from £115 / night

£684 / week

Book Book View

from £115 / night

(8) Excellent 

1 / 55

Berkshires / North Egremont

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Ask owner if suitable for children;
 …see more

from £145 / night

£955 / week

Book Book View

from £145 / night

1 / 27

Berkshires / North Adams

3 15 Min stay varies

  • 3 bedrooms
  • Sleeps 15
  • Min stay varies
Key info: Ski; Child friendly ; Car not necessary;
 …see more

from £123 / night

£611 - £2321 / week

Book Book View

from £123 / night

(2) Excellent 

1 / 9

Massachusetts / Seekonk

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 8 km; Swimming pool; Not suitable for children;
 …see more

from £172 / night

£957 / week

Book Book View

from £172 / night

1 / 25

Berkshires / Lanesboro

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Pet friendly;
 …see more

from £149 / night

£1042 / week

Book Book View

from £149 / night

1 / 11

Falmouth / Waquoit

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; No pets allowed;
 …see more

from £230 / night

£1146 / week

Book Book View

from £230 / night

1 / 14

Falmouth / Teaticket

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Pet friendly;
 …see more

from £84 / night

£583 / week

Book Book View

from £84 / night

(141) Excellent 

1 / 20

Cavalier Cottage B&B - Shelburne Falls b&b sleeps 5

Massachusetts / Shelburne Falls

1 5 2 nights min stay

  • 1 bedroom
  • Sleeps 5
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 0 km; Child friendly ;
Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without t  …see more

from £107 / night

£674 - £1075 / week

Book Book View

from £107 / night

1 / 16

Cape Cod / Wellfleet

3 7 7 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 5 km; Child friendly ;
 …see more

from £138 / night

£962 - £1096 / week

Book Book View

from £138 / night

(1) Excellent 

1 / 11

Massachusetts / Seekonk

3 6 1 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car not necessary;
 …see more

from £76 / night

£530 - £1491 / week

Book Book View

from £76 / night

1 / 21

Massachusetts / Newburyport

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Child friendly ;
 …see more

from £191 / night

£1336 / week

Book Book View

from £191 / night

1 / 21

Massachusetts / Acushnet

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; No pets allowed;
 …see more

from £142 / night

£989 - £1523 / week

Book Book View

from £142 / night

1 / 27

Berkshires / Tyringham

3 6 2 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Ask owner if suitable for children; Ask about pets;
 …see more

from £191 / night

£764 / week

Book Book View

from £191 / night

(12) Excellent 

1 / 15

Massachusetts / Plymouth

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Suitable for children age 5+;
 …see more

from £119 / night

£745 - £1161 / week

Book Book View

from £119 / night

(7) Very Good 

1 / 4

Cape Cod / Eastham

Studio 2 3 nights min stay

  • Studio
  • Sleeps 2
  • 3 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Child friendly ;
 …see more

from £62 / night

£428 / week

Book Book View

from £62 / night

1 / 24

Bourne / Sagamore Beach

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 8 km; Child friendly ;
 …see more

from £306 / night

£2138 - £2939 / week

Book Book View

from £306 / night

(2) Very Good 

1 / 23

Massachusetts / Southbridge

2 4 1 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Beach / lakeside relaxation; Nearest beach 8 km; Child friendly ;
 …see more

from £107 / night

£439 / week

Book Book View

from £107 / night

(3) Excellent 

1 / 32

Massachusetts / New Salem

4 14 2 nights min stay

  • 4 bedrooms
  • Sleeps 14
  • 2 nights min stay
Key info: Nearest beach 5 km; Child friendly ; Car essential;
 …see more

from £195 / night

£1069 / week

Book Book View

from £195 / night

1 / 17

Berkshires / Williamstown

4 16 3 nights min stay

  • 4 bedrooms
  • Sleeps 16
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
 …see more

from £459 / night

£2749 - £4199 / week

Book Book View

from £459 / night

(1) Excellent 

1 / 19

Berkshires / North Egremont

3 8 1 night min stay

  • 3 bedrooms
  • Sleeps 8
  • 1 night min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
 …see more

from £287 / night

£2004 / week

Book Book View

from £287 / night

1 / 23

Berkshires / Lenox

5 14 3 nights min stay

  • 5 bedrooms
  • Sleeps 14
  • 3 nights min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £764 / night

£5344 - £6871 / week

Book Book View

from £764 / night

1 / 4

Cape Cod / Yarmouth

1 4 7 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Nearest beach 3 km; Swimming pool;
 …see more

from £115 / night

£802 / week

Book Book View

from £115 / night

1 / 5

Massachusetts / Newton

3 4 1 night min stay

  • 3 bedrooms
  • Sleeps 4
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £230 / night

£1527 / week

Book Book View

from £230 / night

1 / 22

Cape Cod / Cotuit

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
 …see more

from £382 / night

£2481 - £4313 / week

Book Book View

from £382 / night

1 / 25

Falmouth / Woods Hole

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Car advised;
 …see more

from £322 / night

£2252 - £3016 / week

Book Book View

from £322 / night

1 / 21

Berkshires / Monterey

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 2 km; Ski;
 …see more

from £210 / night

£1146 - £2550 / week

Book Book View

from £210 / night

(16) Very Good 

1 / 24

Hampshire County / Plainfield

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Nearest beach 0.5 km; Ski;
 …see more

from £162 / night

£1088 - £1465 / week

Book Book View

from £162 / night

1 / 9

Cape Cod / Centerville

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
 …see more

from £273 / night

£1909 / week

Book Book View

from £273 / night

1 / 8

Cape Cod / Yarmouth Port

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 3 km; Not suitable for children; Car advised;
 …see more

from £77 / night

£535 / week

Book Book View

from £77 / night

Top Destination reviews

Affordable Luxury -3bd/3ba -$2,300 w/Linens Incl
A fabulous home from home in Cape Cod with beautiful beach close by and access to shared pool, loved it!!!

We have had a brilliant stay in a lovely home on Cape Cod. A very well equipped house close to a beautiful sandy beach and with access to a shared pool. Owners were extremely accommodating, giving lots of help with bike hire etc. Ideally situated for … see more
New lux. Apt.private roof deck harbor/skyline
Fabulous Apartment

I cannot recommend this enough. The apartment was exactly as described, only better. Very clean, new, spacious. All facilities were there and more. Pure luxury stay. Theresa, the owner, emailed me with directions which were perfect. The restaurant … see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page