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:22 June - 20 July
Image gallery for Hidden Gem! Clean & Cozy and Family Friendly!
9.69.6 out of 10, Exceptional, (65 reviews)
Exceptional
(65 reviews)
Hidden Gem! Clean & Cozy and Family Friendly!
Horntown
8% off
Price is AU$13,010
AU$13,010
for 28 nights, 1 home
AU$465 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 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 Grande View 2
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Grande View 2
Pylesville
6% off
Price is AU$3,603
AU$3,603
for 28 nights, 1 apartment
AU$129 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 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$7,773
AU$7,773
for 28 nights, 1 apartment
AU$278 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 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 1BR Waterfront cottage with a view of the wild Chincoteague ponies!
9.69.6 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Chincoteague
8% off
Price is AU$15,383
AU$15,383
for 28 nights, 1 cottage
AU$549 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 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 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 Relaxing Retreat – Pet Friendly, Kayak & Canoe Included, Near Bethany Beach
9.69.6 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Relaxing Retreat – Pet Friendly, Kayak & Canoe Included, Near Bethany Beach
Dagsboro
9% off
Price is AU$12,908
AU$12,908
for 28 nights, 1 home
AU$461 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
Image gallery for 2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
9.69.6 out of 10, Exceptional, (52 reviews)
Exceptional
(52 reviews)
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Chincoteague Island
8% off
Price is AU$16,870
AU$16,870
for 28 nights, 1 cottage
AU$602 per night
includes taxes & fees
Image gallery for Spacious waterfront home with amazing views, private pier, fishing and crabbing.
9.49.4 out of 10, Exceptional, (26 reviews)
Exceptional
(26 reviews)
Spacious waterfront home with amazing views, private pier, fishing and crabbing.
Cambridge
18% off
Price is AU$22,671
AU$22,671
for 28 nights, 1 home
AU$810 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$10,296
AU$10,296
for 28 nights, 1 cottage
AU$368 per night
includes taxes & fees
Image gallery for Cozy Cottage with Beach Access
9.89.8 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Cozy Cottage with Beach Access
Annapolis
8% off
Price is AU$16,548
AU$16,548
for 28 nights, 1 home
AU$591 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 Island
8% off
Price is AU$15,203
AU$15,203
for 28 nights, 1 cottage
AU$543 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$17,435
AU$17,435
for 28 nights, 1 home
AU$623 per night
includes taxes & fees
Image gallery for 1-Bedroom Bayside Canal front Condo. In the heart of downtown OC.
8.68.6 out of 10, Excellent, (11 reviews)
Excellent
(11 reviews)
1-Bedroom Bayside Canal front Condo. In the heart of downtown OC.
Ocean City
8% off
Price is AU$7,220
AU$7,220
for 28 nights, 1 apartment
AU$258 per night
includes taxes & fees
Image gallery for Adorable beach cottage
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Adorable beach cottage
Ocean Pines
12% off
Price is AU$12,651
AU$12,651
for 28 nights, 1 home
AU$452 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.