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:22 June - 20 July
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$7,707
AU$7,707
for 28 nights, 1 cottage
AU$275 per night
includes taxes & fees
Image gallery for Beachside Retreat for 4 – Walk to Buckroe Beach!
9.49.4 out of 10, Exceptional, (28 reviews)
Exceptional
(28 reviews)
Beachside Retreat for 4 – Walk to Buckroe Beach!
Hampton
24% off
Price is AU$5,868
AU$5,868
for 28 nights, 1 home
AU$210 per night
includes taxes & fees
Image gallery for Poquoson 4 bed, 2 bath! Great Langley Access!
8.88.8 out of 10, Excellent, (5 reviews)
Excellent
(5 reviews)
Poquoson 4 bed, 2 bath! Great Langley Access!
Poquoson
38% off
Price is AU$11,504
AU$11,504
for 28 nights, 1 home
AU$411 per night
includes taxes & fees
Image gallery for Cottage at Goose Neck Point
1010 out of 10, Exceptional, (39 reviews)
Exceptional
(39 reviews)
Cottage at Goose Neck Point
Royal Oak
26% off
Price is AU$15,700
AU$15,700
for 28 nights, 1 cottage
AU$561 per night
includes taxes & fees
Image gallery for Buckroe Beach Hideaway - Walk to the Beach!
9.89.8 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Buckroe Beach Hideaway - Walk to the Beach!
Hampton
33% off
Price is AU$7,615
AU$7,615
for 28 nights, 1 home
AU$272 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$16,216
AU$16,216
for 28 nights, 1 apartment
AU$579 per night
includes taxes & fees
Image gallery for Olde Hampton, right in the center of Hampton Roads 1
9.89.8 out of 10, Exceptional, (17 reviews)
Exceptional
(17 reviews)
Olde Hampton, right in the center of Hampton Roads 1
Hampton
18% off
Price is AU$6,938
AU$6,938
for 28 nights, 1 home
AU$248 per night
includes taxes & fees
Image gallery for New Island Home on the Chesapeake Bay Sunsets
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
New Island Home on the Chesapeake Bay Sunsets
Church Creek
17% off
Price is AU$22,330
AU$22,330
for 28 nights, 1 home
AU$798 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$8,649
AU$8,649
for 28 nights, 1 home
AU$309 per night
includes taxes & fees
Image gallery for 3BR Hampton Home, Central to HU, and Colosseum!
9.09.0 out of 10, Wonderful, (4 reviews)
Wonderful
(4 reviews)
3BR Hampton Home, Central to HU, and Colosseum!
Hampton
28% off
Price is AU$8,528
AU$8,528
for 28 nights, 1 home
AU$305 per night
includes taxes & fees
Image gallery for Charming 3BDR Bungalow Near Annapolis
9.69.6 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Charming 3BDR Bungalow Near Annapolis
Riva
12% off
Price is AU$11,781
AU$11,781
for 28 nights, 1 home
AU$421 per night
includes taxes & fees
Image gallery for Perfect Waterview Cottage - St. Michaels Getaway
9.89.8 out of 10, Exceptional, (119 reviews)
Exceptional
(119 reviews)
Perfect Waterview Cottage - St. Michaels Getaway
Wittman
21% off
Price is AU$9,133
AU$9,133
for 28 nights, 1 cottage
AU$326 per night
includes taxes & fees
Image gallery for Guest Quarters at the Inn - 102
9.69.6 out of 10, Exceptional, (25 reviews)
Exceptional
(25 reviews)
Guest Quarters at the Inn - 102
North Beach
18% off
Price is AU$6,984
AU$6,984
for 28 nights, 1 apartment
AU$249 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$9,374
AU$9,374
for 28 nights, 1 apartment
AU$335 per night
includes taxes & fees
Image gallery for Cute Wythe Two Bedroom at Robinson Park
9.69.6 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Cute Wythe Two Bedroom at Robinson Park
Hampton
25% off
Price is AU$8,708
AU$8,708
for 28 nights, 1 home
AU$311 per night
includes taxes & fees
Image gallery for Charming 2-bedroom cottage in tranquil Reedville
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Charming 2-bedroom cottage in tranquil Reedville
Reedville
8% off
Price is AU$8,718
AU$8,718
for 28 nights, 1 cottage
AU$311 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$20,622
AU$20,622
for 28 nights, 1 home
AU$737 per night
includes taxes & fees
Image gallery for Beautiful Retreat Located in Rock Hall - walk to everything!
1010 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Beautiful Retreat Located in Rock Hall - walk to everything!
Rock Hall
28% off
Price is AU$14,804
AU$14,804
for 28 nights, 1 home
AU$529 per night
includes taxes & fees
Image gallery for Charming Home located minutes from the Naval Academy and Downtown Annapolis
9.69.6 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Charming Home located minutes from the Naval Academy and Downtown Annapolis
Annapolis
12% off
Price is AU$21,202
AU$21,202
for 28 nights, 1 home
AU$757 per night
includes taxes & fees
Image gallery for Olde Hampton, right in the center of Hampton Roads 2
7.67.6 out of 10, Good, (5 reviews)
Good
(5 reviews)
Olde Hampton, right in the center of Hampton Roads 2
Hampton
20% off
Price is AU$6,685
AU$6,685
for 28 nights, 1 home
AU$239 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
34% off
Price is AU$11,529
AU$11,529
for 28 nights, 1 home
AU$412 per night
includes taxes & fees
Image gallery for Love Point Waterfront Home....Chesapeake Bay views....Pets OK
9.49.4 out of 10, Exceptional, (118 reviews)
Exceptional
(118 reviews)
Love Point Waterfront Home....Chesapeake Bay views....Pets OK
Stevensville
9% off
Price is AU$18,461
AU$18,461
for 28 nights, 1 home
AU$659 per night
includes taxes & fees
Image gallery for Cute Space Near TownCenter 15 Minutes from Beaches
8.88.8 out of 10, Excellent, (12 reviews)
Excellent
(12 reviews)
Cute Space Near TownCenter 15 Minutes from Beaches
Virginia Beach
8% off
Price is AU$7,414
AU$7,414
for 28 nights, 1 apartment
AU$265 per night
includes taxes & fees
Image gallery for Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Bayview Cottage 2 BR +Off./Priv Beach/Hot Tub/Deck
Huntingtown
9% off
Price is AU$18,312
AU$18,312
for 28 nights, 1 cottage
AU$654 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.