Holiday rentals near Sheep Pond
We found 3,257 holiday rentals — enter your dates for availability
Choose the right holiday rental that's close to Sheep Pond. Holiday homes offer the amenities that you expect for your family, friends or furry companion, such as parking and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Sheep Pond
Showing deals for:18 Jul - 25 Jul
Image gallery for Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Private Beach on Pond, Linens Included, Kayak & Canoe. All Rooms w/ Pond Views!
South Chatham, MA
16% off
Price is S$7,790
S$7,790
S$1,113 per night
includes taxes & fees
Image gallery for Beautiful Pet-friendly home-short drive to Red River Beach!
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Beautiful Pet-friendly home-short drive to Red River Beach!
Harwich, MA
7% off
Price is S$4,538
S$4,538
S$648 per night
includes taxes & fees
Image gallery for Cabin19: Nestled In The Pines In The Heart Of Cape Cod
9.29.2 out of 10 rating
Wonderful
(24 reviews)
Cabin19: Nestled In The Pines In The Heart Of Cape Cod
South Yarmouth, MA
8% off
Price is S$3,388
S$3,388
S$484 per night
includes taxes & fees
Image gallery for Swan River access
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Swan River access
West Dennis, MA
8% off
Price is S$7,114
S$7,114
S$1,016 per night
includes taxes & fees
Image gallery for Great Cape Cod Getaway!
1010 out of 10 rating
Exceptional
(6 reviews)
Great Cape Cod Getaway!
Harwich, MA
8% off
Price is S$4,981
S$4,981
S$712 per night
includes taxes & fees
Image gallery for 4 miles to beaches & 1 mile to lakes! Family friendly, Central A/C, full kitchen
9.69.6 out of 10 rating
Exceptional
(20 reviews)
4 miles to beaches & 1 mile to lakes! Family friendly, Central A/C, full kitchen
Orleans, MA
8% off
Price is S$20,024
S$20,024
S$2,861 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
(73 reviews)
Waterfront, Amazing Sunsets, Dock, Fishing and a Small Beach, 1 Bedroom Sleeps 3
West Dennis, MA
8% off
Price is S$3,515
S$3,515
S$502 per night
includes taxes & fees
Image gallery for 2-Nestled In The Pines In The Heart Of Cape Cod
8.08.0 out of 10 rating
Very good
(5 reviews)
2-Nestled In The Pines In The Heart Of Cape Cod
South Yarmouth, MA
8% off
Price is S$1,833
S$1,833
S$262 per night
includes taxes & fees
Image gallery for 8-Studio Cabin w Kitchen, Enclosed Porch, Bathroom, Sleep2, Beautiful Space,Pool
8.88.8 out of 10 rating
Excellent
(26 reviews)
8-Studio Cabin w Kitchen, Enclosed Porch, Bathroom, Sleep2, Beautiful Space,Pool
South Yarmouth, MA
8% off
Price is S$2,679
S$2,679
S$383 per night
includes taxes & fees
Image gallery for Cozy recently renovated cottage on private 2+ acers of wooded paradise.
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy recently renovated cottage on private 2+ acers of wooded paradise.
Brewster, MA
8% off
Price is S$5,494
S$5,494
S$785 per night
includes taxes & fees
Image gallery for Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.
1010 out of 10 rating
Exceptional
(6 reviews)
Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.
Orleans, MA
7% off
Price is S$2,844
S$2,844
S$406 per night
includes taxes & fees
Image gallery for Private Road - Near Bike Trail & Beaches
9.49.4 out of 10 rating
Exceptional
(29 reviews)
Private Road - Near Bike Trail & Beaches
Eastham, MA
7% off
Price is S$3,012
S$3,012
S$430 per night
includes taxes & fees
Image gallery for Charming Quiet Country Cabin, Heatd Salt Pool, 1mile to Beach, Walk to Mini Golf
9.29.2 out of 10 rating
Wonderful
(43 reviews)
Charming Quiet Country Cabin, Heatd Salt Pool, 1mile to Beach, Walk to Mini Golf
South Yarmouth, MA
8% off
Price is S$3,498
S$3,498
S$500 per night
includes taxes & fees
Image gallery for Cabin Sleeps 5, LOCATION! Beaches, Pool, Golf, Fishing, Waterpark. Good Pets ok!
8.88.8 out of 10 rating
Excellent
(13 reviews)
Cabin Sleeps 5, LOCATION! Beaches, Pool, Golf, Fishing, Waterpark. Good Pets ok!
South Yarmouth, MA
8% off
Price is S$4,036
S$4,036
S$577 per night
includes taxes & fees
Image gallery for Cabin5: Nestled In The Pines In The Heart Of Cape Cod
9.09.0 out of 10 rating
Wonderful
(36 reviews)
Cabin5: Nestled In The Pines In The Heart Of Cape Cod
South Yarmouth, MA
8% off
Price is S$3,098
S$3,098
S$443 per night
includes taxes & fees
Image gallery for #4Charming Cabin for 2 w pool. Near beaches and sites
8.68.6 out of 10 rating
Excellent
(45 reviews)
#4Charming Cabin for 2 w pool. Near beaches and sites
South Yarmouth, MA
8% off
Price is S$2,259
S$2,259
S$323 per night
includes taxes & fees
Image gallery for Cabin1: Nestled In The Pines In The Heart Of Cape Cod
8.28.2 out of 10 rating
Very good
(15 reviews)
Cabin1: Nestled In The Pines In The Heart Of Cape Cod
South Yarmouth, MA
8% off
Price is S$2,251
S$2,251
S$322 per night
includes taxes & fees
Image gallery for Avoid Renters Remorse, Book Your Next Getaway Now!
9.49.4 out of 10 rating
Exceptional
(14 reviews)
Avoid Renters Remorse, Book Your Next Getaway Now!
Harwich Port, Massachusetts
7% off
Price is S$9,065
S$9,065
S$1,295 per night
includes taxes & fees
Image gallery for Family Ready Cabin for 6, 3 BRs, 2 baths, Pool, 1 mile to Beaches, Pet ok, FUN!
9.29.2 out of 10 rating
Wonderful
(27 reviews)
Family Ready Cabin for 6, 3 BRs, 2 baths, Pool, 1 mile to Beaches, Pet ok, FUN!
South Yarmouth, MA
8% off
Price is S$4,280
S$4,280
S$611 per night
includes taxes & fees
Image gallery for Private Cape Cod Cottage. Walk to Ellis Landing Beach!
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster, MA
8% off
Price is S$4,972
S$4,972
S$710 per night
includes taxes & fees
Image gallery for Great Couples Summer Getaway
1010 out of 10 rating
Exceptional
(61 reviews)
Great Couples Summer Getaway
Brewster, MA
7% off
Price is S$2,347
S$2,347
S$335 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Sheep Pond
Tranquility Awaits - a quiet, secluded spot amidst trees and gardens
Sleeps 4 · 2 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
19 reviews(19 reviews)
Pond Perch: 239-B Brewster Pond Front Perfection, Walk to Private Beach
Sleeps 12 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Homeport Harwich by the Lakes w/ 3 Kayak's
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Pond Front Home with Private Dock!
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
42 reviews(42 reviews)
Comfortable 3+ Bedroom Home Near Pleasant Bay (1472)
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
NEW 2025! Family friendly cabin in Harwich, water peek & walk to private beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
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