Eastern Shore 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 Eastern Shore. 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 Eastern Shore 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 - Eastern Shore
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 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 Station House East: Upscale Loft in the Historic District Cambridge, MD
1010 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Station House East: Upscale Loft in the Historic District Cambridge, MD
Cambridge
13% off
Price is AU$6,860
AU$6,860
for 28 nights, 1 apartment
AU$245 per night
includes taxes & fees
Image gallery for Cottage at Goose Neck Point
1010 out of 10, Exceptional, (40 reviews)
Exceptional
(40 reviews)
Cottage at Goose Neck Point
Royal Oak
26% off
Price is AU$15,208
AU$15,208
for 28 nights, 1 cottage
AU$543 per night
includes taxes & fees
Image gallery for Salisbury Cottage
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Salisbury Cottage
Salisbury
22% off
Price is AU$11,548
AU$11,548
for 28 nights, 1 home
AU$412 per night
includes taxes & fees
Image gallery for Salisbury Hideaway
1010 out of 10, Exceptional, (21 reviews)
Exceptional
(21 reviews)
Salisbury Hideaway
Salisbury
22% off
Price is AU$8,259
AU$8,259
for 28 nights, 1 home
AU$295 per night
includes taxes & fees
Image gallery for Cozy Private Apt 10 Minutes from Ocean city MD Beaches !
8.48.4 out of 10, Very good, (10 reviews)
Very good
(10 reviews)
Cozy Private Apt 10 Minutes from Ocean city MD Beaches !
Berlin
8% off
Price is AU$7,329
AU$7,329
for 28 nights, 1 apartment
AU$262 per night
includes taxes & fees
Image gallery for New Island Home on the Chesapeake Bay Sunsets
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
New Island Home on the Chesapeake Bay Sunsets
Church Creek
18% off
Price is AU$20,920
AU$20,920
for 28 nights, 1 home
AU$747 per night
includes taxes & fees
Image gallery for Makai Sunset Cove all-season indoor pool
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Makai Sunset Cove all-season indoor pool
Ocean City
11% off
Price is AU$13,709
AU$13,709
for 28 nights, 1 apartment
AU$490 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 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 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 Waterfront Chesapeake Bay Retreat.
9.29.2 out of 10, Wonderful, (14 reviews)
Wonderful
(14 reviews)
Waterfront Chesapeake Bay Retreat.
Bivalve
27% off
Price is AU$8,000
AU$8,000
for 28 nights, 1 home
AU$286 per night
includes taxes & fees
Image gallery for Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
1010 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fishing Creek
10% off
Price is AU$9,904
AU$9,904
for 28 nights, 1 cottage
AU$354 per night
includes taxes & fees
Image gallery for Family Getaway- Beautiful & spacious 4 Bdrm Historic Home with a modern touch!
9.29.2 out of 10, Wonderful, (15 reviews)
Wonderful
(15 reviews)
Family Getaway- Beautiful & spacious 4 Bdrm Historic Home with a modern touch!
Salisbury
9% off
Price is AU$16,893
AU$16,893
for 28 nights, 1 home
AU$603 per night
includes taxes & fees
Image gallery for Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman
8% off
Price is AU$14,719
AU$14,719
for 28 nights, 1 cottage
AU$526 per night
includes taxes & fees
Image gallery for Sun of the Beach Listing #2
9.89.8 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Sun of the Beach Listing #2
Ocean City
8% off
Price is AU$14,837
AU$14,837
for 28 nights, 1 apartment
AU$530 per night
includes taxes & fees
Image gallery for The Old Crab House Bayfront Pool
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
The Old Crab House Bayfront Pool
Ocean City
10% off
Price is AU$8,963
AU$8,963
for 28 nights, 1 home
AU$320 per night
includes taxes & fees
Image gallery for Coastal Horizon Haven @ the Makai
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Coastal Horizon Haven @ the Makai
Ocean City
11% off
Price is AU$11,226
AU$11,226
for 28 nights, 1 apartment
AU$401 per night
includes taxes & fees
Image gallery for Simple Steps to the Ocean!
9.89.8 out of 10, Exceptional, (54 reviews)
Exceptional
(54 reviews)
Simple Steps to the Ocean!
Ocean City
8% off
Price is AU$11,760
AU$11,760
for 28 nights, 1 apartment
AU$420 per night
includes taxes & fees
Image gallery for Tiburon Tide Retreat
8.08.0 out of 10, Very good, (1 review)
Very good
(1 review)
Tiburon Tide Retreat
Ocean City
11% off
Price is AU$11,450
AU$11,450
for 28 nights, 1 apartment
AU$409 per night
includes taxes & fees
Image gallery for Fabulous One Bedroom Ocean Front , Clean Comfortable , Great Building with Pool
1010 out of 10, Exceptional, (98 reviews)
Exceptional
(98 reviews)
Fabulous One Bedroom Ocean Front , Clean Comfortable , Great Building with Pool
Ocean City
8% off
Price is AU$17,961
AU$17,961
for 28 nights, 1 apartment
AU$641 per night
includes taxes & fees
Image gallery for Beach & Boardwalk just a few steps away. Super clean+ sanitized!
9.69.6 out of 10, Exceptional, (81 reviews)
Exceptional
(81 reviews)
Beach & Boardwalk just a few steps away. Super clean+ sanitized!
Ocean City
8% off
Price is AU$14,837
AU$14,837
for 28 nights, 1 apartment
AU$530 per night
includes taxes & fees
Image gallery for Wave Watcher's Condo - Steps to the beach!
9.89.8 out of 10, Exceptional, (9 reviews)
Exceptional
(9 reviews)
Wave Watcher's Condo - Steps to the beach!
Ocean City
11% off
Price is AU$19,394
AU$19,394
for 28 nights, 1 home
AU$693 per night
includes taxes & fees
Image gallery for Oceanfront condo in North OC with amazing views!
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Oceanfront condo in North OC with amazing views!
Ocean City
17% off
Price is AU$11,103
AU$11,103
for 28 nights, 1 apartment
AU$397 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 Eastern Shore
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.
Eastern Shore 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 Eastern Shore 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 Eastern Shore
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 Eastern Shore 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 Eastern Shore
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Eastern Shore with flexible cancellation policies.