Holiday rentals near Great Island Trail
We found 4,428 holiday rentals — enter your dates for availability
If you are looking to stay near Great Island Trail, scroll through and discover private holiday rentals to find the perfect home base for your trip. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll have the amenities that you expect and more, which might include parking and a hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Great Island Trail
Showing deals for:21 Nov - 28 Nov
Image gallery for Chatham 3 Bedroom/2 Bath Retreat
9.09.0 out of 10 rating
Wonderful
(46 reviews)
Chatham 3 Bedroom/2 Bath Retreat
Chatham, MA
15% off
Price is NZ$3,979
NZ$3,979
NZ$568 per night
includes taxes & fees
Image gallery for Families: Enjoy Harwich, Pool, Large Hot Tub & AC!
9.49.4 out of 10 rating
Exceptional
(10 reviews)
Families: Enjoy Harwich, Pool, Large Hot Tub & AC!
Harwich, MA
8% off
Price is NZ$14,832
NZ$14,832
NZ$2,119 per night
includes taxes & fees
Image gallery for Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
9.69.6 out of 10 rating
Exceptional
(25 reviews)
Steps to private Beach, Golf Course, AC, tandem Kayak for Guests
South Yarmouth, MA
7% off
Price is NZ$2,227
NZ$2,227
NZ$318 per night
includes taxes & fees
Image gallery for Renovated, modern Chatham beach house with lots of cozy charm
9.89.8 out of 10 rating
Exceptional
(36 reviews)
Renovated, modern Chatham beach house with lots of cozy charm
South Chatham, MA
7% off
Price is NZ$5,300
NZ$5,300
NZ$757 per night
includes taxes & fees
Image gallery for Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf
1010 out of 10 rating
Exceptional
(27 reviews)
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf
Brewster, MA
7% off
Price is NZ$7,554
NZ$7,554
NZ$1,079 per night
includes taxes & fees
Image gallery for Private Cape Rental 1 Mile from the Beach!
1010 out of 10 rating
Exceptional
(22 reviews)
Private Cape Rental 1 Mile from the Beach!
East Dennis, MA
7% off
Price is NZ$8,283
NZ$8,283
NZ$1,183 per night
includes taxes & fees
Image gallery for Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
1010 out of 10 rating
Exceptional
(74 reviews)
Clean and Quiet cottage 1/2 mile to Cooks Brook and Sunken Meadow Beach
Eastham, MA
7% off
Price is NZ$2,323
NZ$2,323
NZ$332 per night
includes taxes & fees
Image gallery for Cozy Cape Cottage
9.09.0 out of 10 rating
Wonderful
(19 reviews)
Cozy Cape Cottage
Brewster, MA
8% off
Price is NZ$3,176
NZ$3,176
NZ$454 per night
includes taxes & fees
Image gallery for Classic Bayside cottage, Near Northside Beaches, Private, Close to Sesuit harbor
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Classic Bayside cottage, Near Northside Beaches, Private, Close to Sesuit harbor
East Dennis, MA
7% off
Price is NZ$3,344
NZ$3,344
NZ$478 per night
includes taxes & fees
Image gallery for Come enjoy Orleans and Chatham
1010 out of 10 rating
Exceptional
(17 reviews)
Come enjoy Orleans and Chatham
Orleans, MA
8% off
Price is NZ$3,861
NZ$3,861
NZ$552 per night
includes taxes & fees
Image gallery for Amazing location! Quiet, picturesque neighborhood!
1010 out of 10 rating
Exceptional
(112 reviews)
Amazing location! Quiet, picturesque neighborhood!
Orleans, MA
7% off
Price is NZ$3,702
NZ$3,702
NZ$529 per night
includes taxes & fees
Image gallery for Big House in Heart of Cape. Close to Everything!
1010 out of 10 rating
Exceptional
(111 reviews)
Big House in Heart of Cape. Close to Everything!
South Dennis, MA
8% off
Price is NZ$3,938
NZ$3,938
NZ$563 per night
includes taxes & fees
Image gallery for Cute Cottage on Bass River in West Dennis
9.69.6 out of 10 rating
Exceptional
(50 reviews)
Cute Cottage on Bass River in West Dennis
West Dennis, MA
7% off
Price is NZ$2,977
NZ$2,977
NZ$425 per night
includes taxes & fees
Image gallery for Private Cape Cod Cottage. Walk to Ellis Landing Beach!
1010 out of 10 rating
Exceptional
(34 reviews)
Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster, MA
8% off
Price is NZ$3,528
NZ$3,528
NZ$504 per night
includes taxes & fees
Image gallery for Waterfront, Amazing Sunsets, Dock, Fishing and a Small Beach, 1 Bedroom Sleeps 3
9.09.0 out of 10 rating
Wonderful
(79 reviews)
Waterfront, Amazing Sunsets, Dock, Fishing and a Small Beach, 1 Bedroom Sleeps 3
West Dennis, MA
8% off
Price is NZ$3,317
NZ$3,317
NZ$474 per night
includes taxes & fees
Image gallery for Chatham Beach Chic 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
1010 out of 10 rating
Exceptional
(77 reviews)
Chatham Beach Chic 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
South Chatham, MA
8% off
Price is NZ$6,947
NZ$6,947
NZ$992 per night
includes taxes & fees
Image gallery for Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
1010 out of 10 rating
Exceptional
(22 reviews)
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
South Chatham, MA
15% off
Price is NZ$4,998
NZ$4,998
NZ$714 per night
includes taxes & fees
Image gallery for Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
9.69.6 out of 10 rating
Exceptional
(68 reviews)
Family Friendly Mid CapeHome•Close to all Beaches• Sleeps 6 •Steps to Kelly Bay
South Dennis, MA
7% off
Price is NZ$3,824
NZ$3,824
NZ$546 per night
includes taxes & fees
Image gallery for VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED
9.89.8 out of 10 rating
Exceptional
(74 reviews)
VILLA at Endicott Village GOLF PRIVILEGES AND VIEW Ocean Edge.LINENS PROVIDED
Brewster, MA
8% off
Price is NZ$6,384
NZ$6,384
NZ$912 per night
includes taxes & fees
Image gallery for Cape Cod Pond Cottage
8.88.8 out of 10 rating
Excellent
(33 reviews)
Cape Cod Pond Cottage
Eastham, MA
8% off
Price is NZ$2,783
NZ$2,783
NZ$398 per night
includes taxes & fees
Image gallery for Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
1010 out of 10 rating
Exceptional
(100 reviews)
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich, MA
7% off
Price is NZ$2,109
NZ$2,109
NZ$301 per night
includes taxes & fees
Image gallery for Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
9.69.6 out of 10 rating
Exceptional
(36 reviews)
Ocean views, path to beach, short walk to lighthouse and town, sleeps 12
Chatham, MA
8% off
Price is NZ$66,632
NZ$66,632
NZ$9,519 per night
includes taxes & fees
Image gallery for LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK
1010 out of 10 rating
Exceptional
(83 reviews)
LUXURIOUS DIRECT OCEANFRONT,PRIVATE BEACH,AC,2BD2BA,BONUS LOFT,END UNIT,KAYAK
North Truro, MA
7% off
Price is NZ$6,721
NZ$6,721
NZ$960 per night
includes taxes & fees
Image gallery for Summer home in Harwich: 3 bedrooms, 2 baths and a 20x20 deck to enjoy!
1010 out of 10 rating
Exceptional
(23 reviews)
Summer home in Harwich: 3 bedrooms, 2 baths and a 20x20 deck to enjoy!
Harwich, MA
7% off
Price is NZ$4,391
NZ$4,391
NZ$627 per night
includes taxes & fees
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Find the best place to stay - Great Island Trail
Tranquil 3-Bedroom Truro Cabin on Corn Hill – Steps to Bay, Stunning Views!
Sleeps 8 · 3 bedrooms · 1 bathroom
UPDATED & IMMACULATE HOME! Walk to beach, a/c, WiFi, fire pit!
Sleeps 8 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Family Beach House Close to Bay Beaches, Ponds
Sleeps 8 · 4 bedrooms · 1+ bathroom
9.69.6 out of 10
Exceptionalexceptional
10 reviews(10 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value