Holiday rentals near Sheep Pond
We found 3,388 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:19 Sept - 26 Sept
Image gallery for Stunning Beach Retreat Walk to Chatham Bars Inn, & Town
1010 out of 10 rating
Exceptional
(19 reviews)
Stunning Beach Retreat Walk to Chatham Bars Inn, & Town
Chatham, MA
8% off
Price is AU$20,269
AU$20,269
AU$2,896 per night
includes taxes & fees
Image gallery for CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
9.89.8 out of 10 rating
Exceptional
(19 reviews)
CHATHAM WATER FRONT/VIEW HOUSE FIRST TIME RENTAL
Chatham, MA
8% off
Price is AU$10,544
AU$10,544
AU$1,506 per night
includes taxes & fees
Image gallery for Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house
1010 out of 10 rating
Exceptional
(12 reviews)
Featured in Boston Globe- fully renovated cape w/ pool & modern barn pool house
Orleans, MA
8% off
Price is AU$17,061
AU$17,061
AU$2,437 per night
includes taxes & fees
Image gallery for 🌊 BEACHFRONT FAMILY HOME STEPS TO THE OCEAN!
1010 out of 10 rating
Exceptional
(23 reviews)
🌊 BEACHFRONT FAMILY HOME STEPS TO THE OCEAN!
South Yarmouth, MA
8% off
Price is AU$14,903
AU$14,903
AU$2,129 per night
includes taxes & fees
Image gallery for South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
9.49.4 out of 10 rating
Exceptional
(16 reviews)
South Chatham cottage walk to beaches, dining, tennis, shops, bike path.
South Chatham, MA
7% off
Price is AU$2,530
AU$2,530
AU$361 per night
includes taxes & fees
Image gallery for 2-wing home for large/multi-generation family/friends, cul de sac, beach ~ 1 mi.
9.89.8 out of 10 rating
Exceptional
(36 reviews)
2-wing home for large/multi-generation family/friends, cul de sac, beach ~ 1 mi.
South Harwich, MA
7% off
Price is AU$5,952
AU$5,952
AU$850 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 AU$8,214
AU$8,214
AU$1,173 per night
includes taxes & fees
Image gallery for Private, spacious 5 bedroom mini-estate. Prices slashed for one remaining week
1010 out of 10 rating
Exceptional
(19 reviews)
Private, spacious 5 bedroom mini-estate. Prices slashed for one remaining week
Brewster, MA
14% off
Price is AU$7,542
AU$7,542
AU$1,077 per night
includes taxes & fees
Image gallery for Pristine home w/heated salt water pool - 5 NIGHT MIN- MIDWEEK & WEEKLY DISCOUNT
1010 out of 10 rating
Exceptional
(22 reviews)
Pristine home w/heated salt water pool - 5 NIGHT MIN- MIDWEEK & WEEKLY DISCOUNT
Eastham, MA
7% off
Price is AU$11,868
AU$11,868
AU$1,695 per night
includes taxes & fees
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
23% off
Price is AU$4,372
AU$4,372
AU$625 per night
includes taxes & fees
Image gallery for Come enjoy Orleans and Chatham
1010 out of 10 rating
Exceptional
(13 reviews)
Come enjoy Orleans and Chatham
Orleans, MA
8% off
Price is AU$3,513
AU$3,513
AU$502 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
8% off
Price is AU$5,315
AU$5,315
AU$759 per night
includes taxes & fees
Image gallery for 3-bedroom vacation home, 10-minute drive to Cape Cod bayside beaches
9.69.6 out of 10 rating
Exceptional
(14 reviews)
3-bedroom vacation home, 10-minute drive to Cape Cod bayside beaches
Yarmouth Port, MA
8% off
Price is AU$5,284
AU$5,284
AU$755 per night
includes taxes & fees
Image gallery for Immaculately maintained, large beach home with heated swimming pool
9.69.6 out of 10 rating
Exceptional
(23 reviews)
Immaculately maintained, large beach home with heated swimming pool
Eastham, MA
8% off
Price is AU$8,192
AU$8,192
AU$1,170 per night
includes taxes & fees
Image gallery for LOCATION! CABIN sleeps3, 1 mile to BEACH, Heated POOL, Kitchen/Grill, Parking
9.29.2 out of 10 rating
Wonderful
(24 reviews)
LOCATION! CABIN sleeps3, 1 mile to BEACH, Heated POOL, Kitchen/Grill, Parking
South Yarmouth, MA
8% off
Price is AU$1,970
AU$1,970
AU$281 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 AU$13,033
AU$13,033
AU$1,862 per night
includes taxes & fees
Image gallery for Lovely West Harwich Cape on quiet street, large yard, ten minute walk to beach!
1010 out of 10 rating
Exceptional
(43 reviews)
Lovely West Harwich Cape on quiet street, large yard, ten minute walk to beach!
West Harwich, MA
7% off
Price is AU$3,953
AU$3,953
AU$565 per night
includes taxes & fees
Image gallery for LUXURYBEACHHOUSE*walk2beaches*firepit/bikes/fencedyard/kingbed
1010 out of 10 rating
Exceptional
(5 reviews)
LUXURYBEACHHOUSE*walk2beaches*firepit/bikes/fencedyard/kingbed
South Yarmouth, MA
8% off
Price is AU$6,912
AU$6,912
AU$987 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
(24 reviews)
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf
Brewster, MA
8% off
Price is AU$10,762
AU$10,762
AU$1,537 per night
includes taxes & fees
Image gallery for Steps to the beach!
1010 out of 10 rating
Exceptional
(11 reviews)
Steps to the beach!
Dennis Port, MA
8% off
Price is AU$3,879
AU$3,879
AU$554 per night
includes taxes & fees
Image gallery for Fido friendly Walk to Red River Beach - Sleeps 20 - Hot tub - Bring your boat!
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Fido friendly Walk to Red River Beach - Sleeps 20 - Hot tub - Bring your boat!
Harwich Port, MA
8% off
Price is AU$13,564
AU$13,564
AU$1,938 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
(22 reviews)
Summer home in Harwich: 3 bedrooms, 2 baths and a 20x20 deck to enjoy!
Harwich, MA
7% off
Price is AU$3,995
AU$3,995
AU$571 per night
includes taxes & fees
Image gallery for Charming, Comfortable 1-bedroom Condo with Pool Near Bass River
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Charming, Comfortable 1-bedroom Condo with Pool Near Bass River
West Dennis, MA
7% off
Price is AU$2,969
AU$2,969
AU$424 per night
includes taxes & fees
Image gallery for Delightful Cottage for Two
9.09.0 out of 10 rating
Wonderful
(51 reviews)
Delightful Cottage for Two
Chatham, MA
8% off
Price is AU$2,524
AU$2,524
AU$361 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
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 Front Home with Private Dock!
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
45 reviews(45 reviews)
Bright and Stylish artist owned house with new central A/C and appliances
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
18 reviews(18 reviews)
Great Home With Large Yard 300 Yards To Sheep's Pond (2277)
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Cozy 1 bedroom with fenced in yard, porch and association lake beach access
Sleeps 2 · 1 bedroom · 1 bathroom
Escape to Cape Cod in Our Quaint Cottage - Casa 72
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
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