Chesapeake Bay long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Chesapeake Bay. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Chesapeake Bay are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Chesapeake Bay
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:10 Aug - 7 Sept
Image gallery for Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
9.09.0 out of 10, Wonderful, (8 reviews)
Wonderful
(8 reviews)
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
17% off
Price is AU$7,500
AU$7,500
for 28 nights, 1 cottage
AU$268 per night
includes taxes & fees
Image gallery for Bonfire by the Creek
9.89.8 out of 10, Exceptional, (87 reviews)
Exceptional
(87 reviews)
Bonfire by the Creek
North East
62% off
Price is AU$3,826
AU$3,826
for 28 nights, 1 home
AU$137 per night
includes taxes & fees
Image gallery for Waterfront with Private Pier and Tranquil Water views!
1010 out of 10, Exceptional, (108 reviews)
Exceptional
(108 reviews)
Waterfront with Private Pier and Tranquil Water views!
Gloucester
9% off
Price is AU$9,595
AU$9,595
for 28 nights, 1 cottage
AU$343 per night
includes taxes & fees
Image gallery for Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!
1010 out of 10, Exceptional, (19 reviews)
Exceptional
(19 reviews)
Minutes to the BEACH! Boat friendly, fire pit, bocci & large yard for famly fun!
Cape Charles
17% off
Price is AU$13,560
AU$13,560
for 28 nights, 1 home
AU$484 per night
includes taxes & fees
Image gallery for Vacation home just 8 minutes drive to Oriole Park at Camden Yards
7.47.4 out of 10, Good, (3 reviews)
Good
(3 reviews)
Vacation home just 8 minutes drive to Oriole Park at Camden Yards
Baltimore
16% off
Price is AU$8,186
AU$8,186
for 28 nights, 1 home
AU$292 per night
includes taxes & fees
Image gallery for Unbelievable beach views for 6
1010 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)
Unbelievable beach views for 6
North Beach
9% off
Price is AU$13,385
AU$13,385
for 28 nights, 1 apartment
AU$478 per night
includes taxes & fees
Image gallery for Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
9.89.8 out of 10, Exceptional, (165 reviews)
Exceptional
(165 reviews)
Harbor Cottage at the Chesapeake Bay - Dog Friendly Beach
St. Leonard
27% off
Price is AU$5,681
AU$5,681
for 28 nights, 1 cottage
AU$203 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10, Exceptional, (121 reviews)
Exceptional
(121 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman
21% off
Price is AU$8,861
AU$8,861
for 28 nights, 1 cottage
AU$316 per night
includes taxes & fees
Image gallery for Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Charming cottage on Chesapeake Bay with private sand beach and 1 acre to play on
Heathsville
18% off
Price is AU$11,409
AU$11,409
for 28 nights, 1 cottage
AU$407 per night
includes taxes & fees
Image gallery for Ocean View Beach House. Sleeps 8 Coastal Luxe. Seabreeze!
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Ocean View Beach House. Sleeps 8 Coastal Luxe. Seabreeze!
Norfolk
8% off
Price is AU$20,251
AU$20,251
for 28 nights, 1 home
AU$723 per night
includes taxes & fees
Image gallery for Love Point Waterfront Home....Chesapeake Bay views....Pets OK
9.49.4 out of 10, Exceptional, (119 reviews)
Exceptional
(119 reviews)
Love Point Waterfront Home....Chesapeake Bay views....Pets OK
Stevensville
9% off
Price is AU$17,472
AU$17,472
for 28 nights, 1 home
AU$624 per night
includes taxes & fees
Image gallery for Cute, Cozy 2-bedroom house in near Annapolis with water access
9.69.6 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
Cute, Cozy 2-bedroom house in near Annapolis with water access
Crownsville
8% off
Price is AU$9,886
AU$9,886
for 28 nights, 1 home
AU$353 per night
includes taxes & fees
Image gallery for The Chesapeake Gray Historical Waterside District 20 mins to Oceanfront
9.49.4 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
The Chesapeake Gray Historical Waterside District 20 mins to Oceanfront
Norfolk
20% off
Price is AU$11,481
AU$11,481
for 28 nights, 1 home
AU$410 per night
includes taxes & fees
Image gallery for Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.89.8 out of 10, Exceptional, (86 reviews)
Exceptional
(86 reviews)
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chestertown
30% off
Price is AU$13,870
AU$13,870
for 28 nights, 1 home
AU$495 per night
includes taxes & fees
Image gallery for Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
9.69.6 out of 10, Exceptional, (140 reviews)
Exceptional
(140 reviews)
Bring the Boat & Bikes to Our in Town Kilmarnock Home from 100 per night. <br>
Kilmarnock
35% off
Price is AU$4,248
AU$4,248
for 28 nights, 1 home
AU$152 per night
includes taxes & fees
Image gallery for Annapolis Tree House Apartment- luxury shower, separate space
1010 out of 10, Exceptional, (18 reviews)
Exceptional
(18 reviews)
Annapolis Tree House Apartment- luxury shower, separate space
Annapolis
8% off
Price is AU$9,114
AU$9,114
for 28 nights, 1 apartment
AU$326 per night
includes taxes & fees
Image gallery for BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
1010 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
BWI, Annapolis, DC, Baltimore, USNA family-sized house with a game room and deck
Millersville
36% off
Price is AU$10,554
AU$10,554
for 28 nights, 1 home
AU$377 per night
includes taxes & fees
Image gallery for West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
West Annapolis Hidden Gem <.75Mile To Navy Stadium <1Mile to Downtown Annapolis
Annapolis
21% off
Price is AU$10,478
AU$10,478
for 28 nights, 1 room
AU$374 per night
includes taxes & fees
Image gallery for Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
9.49.4 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)
Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !
Pasadena
8% off
Price is AU$19,259
AU$19,259
for 28 nights, 1 home
AU$688 per night
includes taxes & fees
Image gallery for 4-bedroom house in beautiful Virginia Beach Downtown
8.08.0 out of 10, Very good, (9 reviews)
Very good
(9 reviews)
4-bedroom house in beautiful Virginia Beach Downtown
Virginia Beach
16% off
Price is AU$10,399
AU$10,399
for 28 nights, 1 home
AU$371 per night
includes taxes & fees
Image gallery for Comfortable and quiet 3-bedroom-walk to downtown
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Comfortable and quiet 3-bedroom-walk to downtown
Havre De Grace
8% off
Price is AU$12,669
AU$12,669
for 28 nights, 1 home
AU$452 per night
includes taxes & fees
Image gallery for Cottage Located on the Patuxent River!
1010 out of 10, Exceptional, (43 reviews)
Exceptional
(43 reviews)
Cottage Located on the Patuxent River!
Prince Frederick
9% off
Price is AU$13,223
AU$13,223
for 28 nights, 1 cottage
AU$472 per night
includes taxes & fees
Image gallery for Pet Friendly Hideaway for 4 Close to Annapolis
6.06.0 out of 10, (1 review)
(1 review)
Pet Friendly Hideaway for 4 Close to Annapolis
Annapolis
8% off
Price is AU$14,585
AU$14,585
for 28 nights, 1 home
AU$521 per night
includes taxes & fees
Image gallery for Quiet Woodland cottage near St. Leonard's Creek
9.89.8 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Quiet Woodland cottage near St. Leonard's Creek
Lusby
9% off
Price is AU$4,196
AU$4,196
for 28 nights, 1 cottage
AU$150 per night
includes taxes & fees
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
Great discounts on monthly rentals in Chesapeake Bay
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Chesapeake Bay Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Chesapeake Bay come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Chesapeake Bay
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Chesapeake Bay with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Chesapeake Bay
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Chesapeake Bay with flexible cancellation policies.