Holiday rentals near The Mainstay
We found 804 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:18 Jul - 25 Jul
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$24,363
NZ$24,363
NZ$3,480 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$7,163
NZ$7,163
NZ$1,023 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
(7 reviews)
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Rock Hall, MD
8% off
Price is NZ$3,379
NZ$3,379
NZ$483 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$11,468
NZ$11,468
NZ$1,638 per night
includes taxes & fees
Image gallery for Recently Renovated Annapolis Home - Conveniently Located
1010 out of 10 rating
Exceptional
(58 reviews)
Recently Renovated Annapolis Home - Conveniently Located
Annapolis, MD
8% off
Price is NZ$6,932
NZ$6,932
NZ$990 per night
includes taxes & fees
Image gallery for Historic District"Crab Cakes and Football"
1010 out of 10 rating
Exceptional
(42 reviews)
Historic District"Crab Cakes and Football"
Annapolis, MD
8% off
Price is NZ$5,537
NZ$5,537
NZ$791 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$7,118
NZ$7,118
NZ$1,017 per night
includes taxes & fees
Image gallery for Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
1010 out of 10 rating
Exceptional
(7 reviews)
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Annapolis, MD
8% off
Price is NZ$17,975
NZ$17,975
NZ$2,568 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$6,207
NZ$6,207
NZ$887 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
8% off
Price is NZ$5,093
NZ$5,093
NZ$728 per night
includes taxes & fees
Image gallery for Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis, MD
8% off
Price is NZ$8,547
NZ$8,547
NZ$1,221 per night
includes taxes & fees
Image gallery for Sailor's Retreat! Perfect home for the getaway weekend. Best location!
1010 out of 10 rating
Exceptional
(17 reviews)
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Annapolis, MD
7% off
Price is NZ$8,002
NZ$8,002
NZ$1,143 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$3,913
NZ$3,913
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
(39 reviews)
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Stevensville, MD
8% off
Price is NZ$8,472
NZ$8,472
NZ$1,210 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$3,084
NZ$3,084
NZ$441 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$9,862
NZ$9,862
NZ$1,409 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$2,629
NZ$2,629
NZ$376 per night
includes taxes & fees
Image gallery for Eastern Shore beach cottage get-away
1010 out of 10 rating
Exceptional
(133 reviews)
Eastern Shore beach cottage get-away
Rock Hall, MD
8% off
Price is NZ$4,911
NZ$4,911
NZ$702 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$11,468
NZ$11,468
NZ$1,638 per night
includes taxes & fees
Image gallery for Steps to Naval Academy, City Dock, and State House
9.89.8 out of 10 rating
Exceptional
(68 reviews)
Steps to Naval Academy, City Dock, and State House
Annapolis, MD
7% off
Price is NZ$6,698
NZ$6,698
NZ$957 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$4,949
NZ$4,949
NZ$707 per night
includes taxes & fees
Image gallery for Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B/1B Apt. Sleeps 4.
1010 out of 10 rating
Exceptional
(6 reviews)
Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B/1B Apt. Sleeps 4.
Annapolis, MD
12% off
Price is NZ$2,803
NZ$2,803
NZ$400 per night
includes taxes & fees
Image gallery for Relax on Kent Island in 3 Bedroom Home w/Waterview
9.89.8 out of 10 rating
Exceptional
(34 reviews)
Relax on Kent Island in 3 Bedroom Home w/Waterview
Stevensville, MD
8% off
Price is NZ$5,258
NZ$5,258
NZ$751 per night
includes taxes & fees
Image gallery for Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
1010 out of 10 rating
Exceptional
(10 reviews)
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Chestertown, MD
12% off
Price is NZ$2,681
NZ$2,681
NZ$383 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)
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
277 reviews(277 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
51 reviews(51 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)
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)
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