Holiday rentals near The Mainstay
We found 824 holiday rentals — enter your dates for availability
Take a look at holiday rentals near The Mainstay that provide the perfect home base for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a fireplace. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - The Mainstay
Showing deals for:1 Aug - 8 Aug
Image gallery for Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
1010 out of 10 rating
Exceptional
(23 reviews)
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
Annapolis, MD
7% off
Price is NZ$24,601
NZ$24,601
NZ$3,514 per night
includes taxes & fees
Image gallery for Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
1010 out of 10 rating
Exceptional
(8 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is NZ$3,381
NZ$3,381
NZ$483 per night
includes taxes & fees
Image gallery for Escape Villa in Downtown Annapolis
1010 out of 10 rating
Exceptional
(7 reviews)
Escape Villa in Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$7,306
NZ$7,306
NZ$1,044 per night
includes taxes & fees
Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
1010 out of 10 rating
Exceptional
(13 reviews)
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall, MD
16% off
Price is NZ$3,076
NZ$3,076
NZ$439 per night
includes taxes & fees
Image gallery for 4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
1010 out of 10 rating
Exceptional
(33 reviews)
4 KING Bedrooms on the Waterfront- FREE Kent Island Sunsets- Near Wedding Venues
Stevensville, MD
8% off
Price is NZ$11,734
NZ$11,734
NZ$1,676 per night
includes taxes & fees
Image gallery for Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
1010 out of 10 rating
Exceptional
(118 reviews)
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Chester, MD
8% off
Price is NZ$5,382
NZ$5,382
NZ$769 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10 rating
Exceptional
(15 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis, MD
12% off
Price is NZ$4,292
NZ$4,292
NZ$613 per night
includes taxes & fees
Image gallery for Recently Renovated Annapolis Home - Conveniently Located
1010 out of 10 rating
Exceptional
(60 reviews)
Recently Renovated Annapolis Home - Conveniently Located
Annapolis, MD
7% off
Price is NZ$6,968
NZ$6,968
NZ$995 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis, MD
8% off
Price is NZ$7,256
NZ$7,256
NZ$1,037 per night
includes taxes & fees
Image gallery for Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
1010 out of 10 rating
Exceptional
(75 reviews)
Waterview with Beach Volleyball! Walk to Marina & Kentmorr Beach Bar and Grill.
Stevensville, MD
8% off
Price is NZ$11,734
NZ$11,734
NZ$1,676 per night
includes taxes & fees
Image gallery for Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Annapolis Charm - Waterfront Private Fishing Dock Pier Near Beach - Navy Academy
Annapolis, MD
8% off
Price is NZ$6,351
NZ$6,351
NZ$907 per night
includes taxes & fees
Image gallery for Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
1010 out of 10 rating
Exceptional
(7 reviews)
Waterfront at "The Landing" in Historic Rock Hall, overlooking marina and pool.
Rock Hall, MD
8% off
Price is NZ$3,914
NZ$3,914
NZ$559 per night
includes taxes & fees
Image gallery for Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
1010 out of 10 rating
Exceptional
(40 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$9,511
NZ$9,511
NZ$1,359 per night
includes taxes & fees
Image gallery for Location Location Location!!!50 Steps from Main Street and all of the action
9.89.8 out of 10 rating
Exceptional
(62 reviews)
Location Location Location!!!50 Steps from Main Street and all of the action
Annapolis, MD
7% off
Price is NZ$5,174
NZ$5,174
NZ$739 per night
includes taxes & fees
Image gallery for Charming 239-year-old former tavern 1 block to water & shops
1010 out of 10 rating
Exceptional
(9 reviews)
Charming 239-year-old former tavern 1 block to water & shops
Annapolis, MD
8% off
Price is NZ$10,045
NZ$10,045
NZ$1,435 per night
includes taxes & fees
Image gallery for House w/Water Views of Rock Creek 2BA 2BA Cottage
1010 out of 10 rating
Exceptional
(26 reviews)
House w/Water Views of Rock Creek 2BA 2BA Cottage
Pasadena, MD
7% off
Price is NZ$3,086
NZ$3,086
NZ$441 per night
includes taxes & fees
Image gallery for Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
9.29.2 out of 10 rating
Wonderful
(33 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Annapolis, MD
8% off
Price is NZ$2,674
NZ$2,674
NZ$382 per night
includes taxes & fees
Image gallery for Cozy Annapolis Cottage
1010 out of 10 rating
Exceptional
(8 reviews)
Cozy Annapolis Cottage
Annapolis, MD
8% off
Price is NZ$5,850
NZ$5,850
NZ$836 per night
includes taxes & fees
Image gallery for Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
1010 out of 10 rating
Exceptional
(38 reviews)
Waterview Home by Kentmorr Marina, Beach Bar & Grill. Close to wedding venues.
Stevensville, MD
8% off
Price is NZ$11,734
NZ$11,734
NZ$1,676 per night
includes taxes & fees
Image gallery for Truly Waterfront Cottage
1010 out of 10 rating
Exceptional
(70 reviews)
Truly Waterfront Cottage
Pasadena, MD
8% off
Price is NZ$2,886
NZ$2,886
NZ$412 per night
includes taxes & fees
Image gallery for The Lazy River House
1010 out of 10 rating
Exceptional
(8 reviews)
The Lazy River House
Chestertown, MD
8% off
Price is NZ$7,598
NZ$7,598
NZ$1,085 per night
includes taxes & fees
Image gallery for In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
9.89.8 out of 10 rating
Exceptional
(9 reviews)
In Town, Rock Hall, Fenced-In Yard, 1 Block to Bay!!
Rock Hall, MD
8% off
Price is NZ$2,970
NZ$2,970
NZ$424 per night
includes taxes & fees
Image gallery for Kent Island Waterfront Cottage
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Kent Island Waterfront Cottage
Stevensville, MD
16% off
Price is NZ$4,197
NZ$4,197
NZ$600 per night
includes taxes & fees
Image gallery for Charming Charles Retreat
1010 out of 10 rating
Exceptional
(7 reviews)
Charming Charles Retreat
Annapolis, MD
7% off
Price is NZ$5,479
NZ$5,479
NZ$783 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Mainstay
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Sleeps 25 · 9 bedrooms · 6+ bathrooms
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Historic Manor House on Beautiful Eastern Shore Estate
Sleeps 13 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
Sleeps 10 · 4 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
47 reviews(47 reviews)
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
278 reviews(278 reviews)
EASTERN SHORE Maryland --2 minute walk to beach; Quintessential beach home
Sleeps 11 · 6 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
105 reviews(105 reviews)
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.
Sleeps 16 · 7 bedrooms · 5+ bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 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