Holiday rentals near The Mainstay
We found 820 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:19 Sept - 26 Sept
Image gallery for House near Patapsco River 2700 square feet
9.49.4 out of 10 rating
Exceptional
(13 reviews)
House near Patapsco River 2700 square feet
Pasadena, MD
8% off
Price is NZ$9,914
NZ$9,914
NZ$1,416 per night
includes taxes & fees
Image gallery for Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
1010 out of 10 rating
Exceptional
(11 reviews)
Creek-Side Bliss: Unwind and Create Lasting Memories at Our Beautiful Retreat
Pasadena, MD
8% off
Price is NZ$9,639
NZ$9,639
NZ$1,377 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$3,337
NZ$3,337
NZ$477 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$7,163
NZ$7,163
NZ$1,023 per night
includes taxes & fees
Image gallery for Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
1010 out of 10 rating
Exceptional
(5 reviews)
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
Annapolis, MD
11% off
Price is NZ$11,908
NZ$11,908
NZ$1,701 per night
includes taxes & fees
Image gallery for Rare find! Chic cottage, salt water heated pool May 15-Oct15.
1010 out of 10 rating
Exceptional
(50 reviews)
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Arnold, MD
12% off
Price is NZ$9,914
NZ$9,914
NZ$1,416 per night
includes taxes & fees
Image gallery for Pasadena, MD close to Annapolis/WDC/Baltimore
1010 out of 10 rating
Exceptional
(35 reviews)
Pasadena, MD close to Annapolis/WDC/Baltimore
Pasadena, MD
11% off
Price is NZ$3,820
NZ$3,820
NZ$546 per night
includes taxes & fees
Image gallery for Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
1010 out of 10 rating
Exceptional
(6 reviews)
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully
Centreville, MD
8% off
Price is NZ$16,304
NZ$16,304
NZ$2,329 per night
includes taxes & fees
Image gallery for Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
1010 out of 10 rating
Exceptional
(5 reviews)
Chesapeake Eastern Shore, Chestertown MD, waterfront with shared pool and dock.
Chestertown, MD
17% off
Price is NZ$4,846
NZ$4,846
NZ$692 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
(14 reviews)
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Annapolis, MD
8% off
Price is NZ$8,053
NZ$8,053
NZ$1,150 per night
includes taxes & fees
Image gallery for Chesapeake Bay Waterfront ARTectural Home
1010 out of 10 rating
Exceptional
(27 reviews)
Chesapeake Bay Waterfront ARTectural Home
Stevensville, MD
8% off
Price is NZ$12,748
NZ$12,748
NZ$1,821 per night
includes taxes & fees
Image gallery for Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
1010 out of 10 rating
Exceptional
(15 reviews)
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall, MD
16% off
Price is NZ$3,036
NZ$3,036
NZ$434 per night
includes taxes & fees
Image gallery for Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.49.4 out of 10 rating
Exceptional
(87 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena, MD
8% off
Price is NZ$6,333
NZ$6,333
NZ$905 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
11% off
Price is NZ$3,373
NZ$3,373
NZ$482 per night
includes taxes & fees
Image gallery for Cozy, unique, historic registered cottage on the Corsica River!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy, unique, historic registered cottage on the Corsica River!
Centreville, MD
8% off
Price is NZ$2,943
NZ$2,943
NZ$420 per night
includes taxes & fees
Image gallery for Beautiful Historic Home With Great Location!
1010 out of 10 rating
Exceptional
(124 reviews)
Beautiful Historic Home With Great Location!
Annapolis, MD
7% off
Price is NZ$6,337
NZ$6,337
NZ$905 per night
includes taxes & fees
Image gallery for Ruby's Sea Glass Cottage near Betterton Beach
1010 out of 10 rating
Exceptional
(22 reviews)
Ruby's Sea Glass Cottage near Betterton Beach
Betterton, MD
9% off
Price is NZ$2,913
NZ$2,913
NZ$416 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$9,916
NZ$9,916
NZ$1,417 per night
includes taxes & fees
Image gallery for Gem in Downtown Annapolis, close to USNA, St. John's College
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Gem in Downtown Annapolis, close to USNA, St. John's College
Annapolis, MD
8% off
Price is NZ$5,491
NZ$5,491
NZ$784 per night
includes taxes & fees
Image gallery for House w/Water Views of Rock Creek 2BA 2BA Cottage
1010 out of 10 rating
Exceptional
(27 reviews)
House w/Water Views of Rock Creek 2BA 2BA Cottage
Pasadena, MD
7% off
Price is NZ$2,436
NZ$2,436
NZ$348 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
(35 reviews)
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
Annapolis, MD
8% off
Price is NZ$2,639
NZ$2,639
NZ$377 per night
includes taxes & fees
Image gallery for Beautiful, spacious waterfront home, an easy walk to historic Chestertown
9.89.8 out of 10 rating
Exceptional
(22 reviews)
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Chestertown, MD
7% off
Price is NZ$15,484
NZ$15,484
NZ$2,212 per night
includes taxes & fees
Image gallery for Truly Waterfront Cottage
1010 out of 10 rating
Exceptional
(74 reviews)
Truly Waterfront Cottage
Pasadena, MD
8% off
Price is NZ$2,849
NZ$2,849
NZ$407 per night
includes taxes & fees
Image gallery for Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
1010 out of 10 rating
Exceptional
(21 reviews)
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 8 with pond view!
Rock Hall, MD
8% off
Price is NZ$4,251
NZ$4,251
NZ$607 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
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
35 reviews(35 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
48 reviews(48 reviews)
Water Front Retreat - Sunrise and Sunset Water Views - Lots of Amenities
Sleeps 8 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
283 reviews(283 reviews)
Grand home located right on Main St, walk to Chesapeake Bay & great restaurants
Sleeps 13 · 5 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
BAYSIDE BUNGALOW
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
39 reviews(39 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