Vacation rentals near Chesapeake Hills Golf Course
We found 268 vacation rentals — enter your dates for availability
If you want to to stay within easy reach of Chesapeake Hills Golf Course, take a look at private vacation rentals to find the perfect one for your trip. Whether you're staying in a vacation rental with your kids or with friends, you'll find the amenities you need and want, such as parking and air conditioning. You'll be able to choose a rental to meet everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Chesapeake Hills Golf Course
Showing deals for:Nov 14 - Nov 21
Image gallery for New Island Home on the Chesapeake Bay Sunsets
1010 out of 10 rating
Exceptional
(7 reviews)
New Island Home on the Chesapeake Bay Sunsets
Church Creek, MD
10% off
Price is CA $615
CA $615
CA $5,598 total
CA $5,598 total
includes taxes & fees
Image gallery for Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
1010 out of 10 rating
Exceptional
(7 reviews)
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge, MD
5% off
Price is CA $318
CA $318
CA $2,812 total
CA $2,812 total
includes taxes & fees
Image gallery for CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
9.49.4 out of 10 rating
Exceptional
(15 reviews)
CH Waterfront Home w/ Dock, Pool, Sandy Beach, Kayaks, 5BR/3.5BA Sleeps up to 16
Cambridge, MD
10% off
Price is CA $1,363
CA $1,363
CA $11,779 total
CA $11,779 total
includes taxes & fees
Image gallery for Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
9.89.8 out of 10 rating
Exceptional
(130 reviews)
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge, MD
10% off
Price is CA $496
CA $496
CA $4,572 total
CA $4,572 total
includes taxes & fees
Image gallery for Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier
1010 out of 10 rating
Exceptional
(12 reviews)
Alpaca Farm on Chesapeake Bay - 86 Private Acres, Heated Pool, Beach, 600' Pier
Cambridge, MD
10% off
Price is CA $1,575
CA $1,575
CA $14,925 total
CA $14,925 total
includes taxes & fees
Image gallery for Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Fish, kayak, bike, and more at this private serene 24-acre waterfront estate.
Cambridge, MD
10% off
Price is CA $481
CA $481
CA $4,199 total
CA $4,199 total
includes taxes & fees
Image gallery for Family and Pet-Friendly, Waterfront with Pier
1010 out of 10 rating
Exceptional
(253 reviews)
Family and Pet-Friendly, Waterfront with Pier
Cambridge, MD
10% off
Price is CA $341
CA $341
CA $2,881 total
CA $2,881 total
includes taxes & fees
Image gallery for Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.89.8 out of 10 rating
Exceptional
(73 reviews)
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Woolford, MD
10% off
Price is CA $990
CA $990
CA $8,865 total
CA $8,865 total
includes taxes & fees
Image gallery for Beautiful Waterfront Retreat in Cambridge!
1010 out of 10 rating
Exceptional
(43 reviews)
Beautiful Waterfront Retreat in Cambridge!
Cambridge, MD
10% off
Price is CA $341
CA $341
CA $3,000 total
CA $3,000 total
includes taxes & fees
Image gallery for Outrigger at Swan Cove Manor
9.09.0 out of 10 rating
Wonderful
(15 reviews)
Outrigger at Swan Cove Manor
Cambridge, MD
10% off
Price is CA $496
CA $496
CA $4,742 total
CA $4,742 total
includes taxes & fees
Image gallery for Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay
1010 out of 10 rating
Exceptional
(48 reviews)
Stunning Waterfront Eastern Shore Home,Pool & Hot Tub,15 Acres,15%off 7day stay
Cambridge, MD
10% off
Price is CA $985
CA $985
CA $8,836 total
CA $8,836 total
includes taxes & fees
Image gallery for Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
1010 out of 10 rating
Exceptional
(77 reviews)
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Cambridge, MD
10% off
Price is CA $1,487
CA $1,487
CA $12,087 total
CA $12,087 total
includes taxes & fees
Image gallery for Waterfront property with private boat ramp and new dock!
9.49.4 out of 10 rating
Exceptional
(13 reviews)
Waterfront property with private boat ramp and new dock!
Cambridge, MD
10% off
Price is CA $310
CA $310
CA $2,671 total
CA $2,671 total
includes taxes & fees
Image gallery for Resort Style Country Living on the Patuxent River
1010 out of 10 rating
Exceptional
(14 reviews)
Resort Style Country Living on the Patuxent River
St. Leonard, MD
10% off
Price is CA $2,230
CA $2,230
CA $18,151 total
CA $18,151 total
includes taxes & fees
Image gallery for WATERFRONT!!! The River's Roost on The Patuxent River
1010 out of 10 rating
Exceptional
(26 reviews)
WATERFRONT!!! The River's Roost on The Patuxent River
St. Leonard, MD
5% off
Price is CA $361
CA $361
CA $3,403 total
CA $3,403 total
includes taxes & fees
Image gallery for Serenity Bay-Spacious House-Private Pool-6 bdrms-5baths-Ask about 2-night stays
9.29.2 out of 10 rating
Wonderful
(17 reviews)
Serenity Bay-Spacious House-Private Pool-6 bdrms-5baths-Ask about 2-night stays
Lexington Park, MD
5% off
Price is CA $644
CA $644
CA $6,133 total
CA $6,133 total
includes taxes & fees
Image gallery for Bayfront Gem w/ Amazing Water Views + Pond!
1010 out of 10 rating
Exceptional
(17 reviews)
Bayfront Gem w/ Amazing Water Views + Pond!
Madison, MD
20% off
Price is CA $536
CA $536
CA $5,329 total
CA $5,329 total
includes taxes & fees
Image gallery for Discover tranquility near Calvert Cliffs
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Discover tranquility near Calvert Cliffs
St. Leonard, MD
37% off
Price is CA $483
CA $483
CA $4,332 total
CA $4,332 total
includes taxes & fees
Image gallery for 5 bedroom, 8 bed, 3 story house a block from beach
9.69.6 out of 10 rating
Exceptional
(15 reviews)
5 bedroom, 8 bed, 3 story house a block from beach
St. Leonard, MD
6% off
Price is CA $456
CA $456
CA $3,986 total
CA $3,986 total
includes taxes & fees
Image gallery for Beach-Front Classic on the Chesapeake Bay
1010 out of 10 rating
Exceptional
(5 reviews)
Beach-Front Classic on the Chesapeake Bay
St. Leonard, MD
5% off
Price is CA $746
CA $746
CA $6,494 total
CA $6,494 total
includes taxes & fees
Image gallery for Cottage Located on the Patuxent River!
1010 out of 10 rating
Exceptional
(39 reviews)
Cottage Located on the Patuxent River!
Prince Frederick, MD
10% off
Price is CA $366
CA $366
CA $2,962 total
CA $2,962 total
includes taxes & fees
Image gallery for Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
1010 out of 10 rating
Exceptional
(16 reviews)
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
St. Leonard, MD
10% off
Price is CA $258
CA $258
CA $2,432 total
CA $2,432 total
includes taxes & fees
Image gallery for Year-Round River Escape with Beach & Indoor Heated Pool, Hot Tub and more!
1010 out of 10 rating
Exceptional
(28 reviews)
Year-Round River Escape with Beach & Indoor Heated Pool, Hot Tub and more!
Hague, VA
10% off
Price is CA $1,229
CA $1,229
CA $10,550 total
CA $10,550 total
includes taxes & fees
Image gallery for 2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
1010 out of 10 rating
Exceptional
(5 reviews)
2 blocks from Bay! Private beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick, MD
20% off
Price is CA $352
CA $352
CA $3,055 total
CA $3,055 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Chesapeake Hills Golf Course
A Hideaway in Hays Beach: Chesapeake Bay, 5G WiFi, 60 Second Walk to Beach
Sleeps 8 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
The Cedar Beach Lodge
Sleeps 10 · 3 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
104 reviews(104 reviews)
Waterfront Cottage in Beautiful Hoopers Island
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
76 reviews(76 reviews)
Belle of the Chesapeake Bay
Sleeps 8 · 4 bedrooms · 3 bathrooms
9.09.0 out of 10
Wonderfulwonderful
14 reviews(14 reviews)
Private Beach Front Getaway at The Sunshine Beach Cottage.
Sleeps 8 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Top rated rentals - Chesapeake Hills Golf Course
Bliss on The Bay
1010 out of 10
Exceptionalexceptional
177 reviews(177 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, yards and more
More for lessMore space, more privacy, more amenities — more value