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144 Rentals In Talbot Area
United States
Maryland
Talbot Area
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Tred Avon River
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Peachblossom Creek
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Maxmore Creek
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Choptank River
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Price
Per Night:
Amenities
Pool
Internet
Washer
Fishing
FirePlace
Wheelchair Access
Non Smoking
Yard
TV
Balcony
Patio
Parking
AC
Microwave
No Pets
Jacuzzi
Pet Allowed
Dishwasher
Kitchen
Sauna
Crib
Smoking Allowed
Grill
ENDLESS SUNSETS ON THE EASTERN BAY
2
3.0
4
Claiborne Maryland Private vacation home
From $676 per night
(USD)
Historic Oxford Waterfront Estate
6
4.0
12
Oxford Maryland Private vacation home
From $1180 per night
(USD)
St. Michael's Premier In-Town Rental with heated pool. Pool closes 10/27
2
2.0
4
St. Michaels Maryland Cottage
From $516 per night
(USD)
20% Off 5 Night Min. Waterfront, Hot Tub, Pool,Minutes to St.Michaels.
5
5.0
10
Royal Oak Maryland Private vacation home
From $857 per night
(USD)
Charming cottage along water with private pier, near St. Michaels Winery
1
2.0
2
Bozman Maryland Cottage
From $322 per night
(USD)
Cottage at Goose Neck Point
1
1.0
2
Royal Oak Maryland Cottage
From $549 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Luxury
5
5.0
10
Royal Oak Maryland Private vacation home
From $2729 per night
(USD)
ST. MICHAELS ESTATE OFFERS WATERFRONT POOL, PIER, DOCK AND 15 ACS PET FRIENDLY
5
5.0
10
Sherwood Maryland Private vacation home
From $1638 per night
(USD)
Private+Cozy-3br+2ba-1mile to Historic Downtown Saint Michaels
3
2.0
6
Saint Michaels Maryland Private vacation home
From $398 per night
(USD)
Large -IN TOWN- Historic House on Harbor in St Michaels - Walk to Everything!
6
3.0
9
St. Michaels Maryland Private vacation home
From $741 per night
(USD)
Stay in the HEART of Saint Michaels!
2
2.0
4
St Michaels Maryland Private vacation home
From $382 per night
(USD)
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
2
1.0
5
St Michaels Maryland Cottage
From $374 per night
(USD)
Two Oysters House 2025 Remodel waterfront w/ pool in St. Michaels
4
3.0
8
St Michaels Maryland Private vacation home
From $821 per night
(USD)
Family Friendly Cottage - Waterfront. Spectacular Sunsets over Chesapeake Bay
3
2.0
5
Tilghman Maryland Private vacation home
From $601 per night
(USD)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
2
2.0
5
Saint Michaels Maryland Cottage
From $413 per night
(USD)
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
5
3.0
10
easton Maryland Private vacation home
From $1203 per night
(USD)
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
6
3.0
10
Easton Maryland Private vacation home
From $843 per night
(USD)
Thorneton Point Estate
6
5.0
12
Easton Maryland Private vacation home
From $998 per night
(USD)
Breathtaking Waterfront Estate
6
4.0
12
Neavitt Maryland Villa
From $967 per night
(USD)
House on the Chesapeake Bay
3
2.0
6
Tilghman Island Maryland Private vacation home
From $678 per night
(USD)
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
8
9.0
12
Sherwood Maryland Private vacation home
From $1583 per night
(USD)
Historic Waterfront Estate with Pool & Pet-Friendly – Perfect for Fall Getaways
5
4.0
10
Oxford Maryland Private vacation home
From $993 per night
(USD)
We still have availability for August to October 2026 STR #22-30
5
4.0
10
Bozman Maryland Private vacation home
From $488 per night
(USD)
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
3
3.0
6
St. Michaels Maryland Private vacation home
From $971 per night
(USD)
Relax or Play on the Choptank River!
1
1.0
2
Trappe Maryland Hotel resort
From $374 per night
(USD)
Luxurious waterfront home - Cèilidh
4
3.0
7
Oxford Maryland Private vacation home
From $1031 per night
(USD)
Minutes from Downtown St. Michael's | Game Room | Pool | Hot Tub | Pickle Ball C
5
4.0
10
Saint Michaels Maryland Private vacation home
From $1539 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Pickle Ball Court | Private Dock | K
5
5.0
10
Easton Maryland Private vacation home
From $1363 per night
(USD)
Tilghman Island Waterfront Retreat with Brand New Pool – Summer 2026!
4
4.0
8
Tilghman Maryland Private vacation home
From $813 per night
(USD)
🌊 Book Now for 15% Off. Waterfront, Dock, Hot Tub, Sandy Beach, Elevator!
4
4.0
8
Royal Oak Maryland Private vacation home
From $568 per night
(USD)
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
3
3.0
6
St. Michaels Maryland Private vacation home
From $924 per night
(USD)
Downtown Oxford | Charming | Pet Friendly
3
2.0
6
Oxford Maryland Private vacation home
From $777 per night
(USD)
Minutes from Downtown St. Michaels | Private Dock | Kayaks
4
3.0
8
Saint Michaels Maryland Private vacation home
From $816 per night
(USD)
Relaxing Waterfront Cottage Near St Michaels, Maryland
2
2.0
4
Wittman Maryland Cottage
From $277 per night
(USD)
LUXURY COASTAL FARMHOUSE WATERFRONT W/ HEATED POOL, DOCK, GOURMET KITCHEN
3
4.0
6
Saint Michaels Maryland Agritourism
From $1593 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Private Dock |
3
2.0
6
Saint Michaels Maryland Private vacation home
From $1023 per night
(USD)
BOOK NOW FOR SPRING & SUMMER DATES.
3
2.0
6
Tilghman Island Maryland Private vacation home
From $533 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
3
2.0
6
Easton Maryland Private vacation home
Click For Pricing
Dollhouse in Central Historic St Michaels
2
1.0
4
St Michaels Maryland Private vacation home
From $329 per night
(USD)
Downtown St. Michaels | Bikes | Kayaks | Private Pier
3
2.0
6
Saint Michaels Maryland Private vacation home
From $1024 per night
(USD)
Baydream Believer
5
4.0
8
Talbot County Maryland Private vacation home
From $1164 per night
(USD)
Waterfront Oyster Farmhouse Built 2018 with Pool/Fence and Dock-23 private acres
4
4.0
8
Wittman Maryland Private vacation home
From $1277 per night
(USD)
St. Michaels Waterfront Home
2
2.0
4
New comb Maryland Private vacation home
From $621 per night
(USD)
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
2
2.0
5
Saint Michaels Maryland Cottage
From $374 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Hot Tub | Kayaks | Privat
5
3.0
10
Easton Maryland Private vacation home
From $1387 per night
(USD)
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
2
2.0
5
St Michaels Maryland Cottage
From $329 per night
(USD)
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
5
3.0
10
Easton Maryland Private vacation home
From $1092 per night
(USD)
Waterfront Cottage, Private Hot Tub, Fire Pit, Pool - perfect Romantic Getaway
2
2.0
4
Easton Maryland Guest house
From $493 per night
(USD)
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
4
2.0
8
Neavitt Maryland Private vacation home
From $856 per night
(USD)
Walk to Everything House
3
1.0
6
Saint Michaels Maryland Private vacation home
From $361 per night
(USD)
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
1
1.0
2
St. Michaels Maryland Cottage
From $630 per night
(USD)
Modern room with walk in shower and kitchenette
1
1.0
2
Trappe Maryland Bed & breakfast
From $349 per night
(USD)
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Eastern Shore MD
1
1.0
2
Oxford Maryland Apart-hotel
From $280 per night
(USD)
Sandaway Suites & Beach Boutique Hotel, Private Beach, Walk to Dining & Shops!
1
1.0
2
Oxford Maryland Hotel
From $333 per night
(USD)
Sandaway Suites & Beach - Full Kitchen & Private Beach Access - Oxford, Maryland
1
1.0
2
Oxford Maryland Apart-hotel
From $333 per night
(USD)
Waterfront Property, kayaks, private dock, near town
3
2.0
6
St. Michaels Maryland Private vacation home
From $900 per night
(USD)
TRUE IN-TOWN ST MICHAELS 6 ACRE WATERFRONT - Heated Pool
5
3.0
8
St Michaels Maryland Private vacation home
From $1246 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
4
3.0
8
Royal Oak Maryland Private vacation home
From $1019 per night
(USD)
Stunning views at WATERFRONT St Michaels area historic home, dog friendly
2
1.0
4
Neavitt Maryland Private vacation home
From $392 per night
(USD)
Perfect Waterview Cottage - St. Michaels Getaway
2
1.0
4
Wittman Maryland Cottage
From $298 per night
(USD)
Overlook on Dun's Cove -- Luxury waterfront hideaway minutes from St. Michaels
2
2.0
4
Sherwood Maryland Private vacation home
From $357 per night
(USD)
Grandview- Main House
4
2.0
17
Bozman Maryland Private vacation home
From $985 per night
(USD)
Secluded Waterfront Property on 3 acres with swimming pool and dock.
4
2.0
8
Bozman Maryland Private vacation home
From $1089 per night
(USD)
Harbor View Suite Talbot County License Number STRN-25-58
1
1.0
2
Saint Michaels Maryland Apartment
From $313 per night
(USD)
Eastern Shore Oasis!
4
3.0
8
Easton Maryland Private vacation home
From $1005 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
4
2.0
8
St. Michaels Maryland Private vacation home
From $1099 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Kayaks | Private Dock | Newly Renova
5
4.0
10
Bozman Maryland Private vacation home
From $1430 per night
(USD)
A Luxury Home located in Easton with Water VIEWS! Close to Oxford/St. Michaels
3
2.0
6
Easton Maryland Private vacation home
From $438 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
4
4.0
8
Easton Maryland Private vacation home
From $2045 per night
(USD)
Eastern Shore Waterside Cottage Near St. Michaels
3
2.0
6
Neavitt Maryland Cottage
From $484 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Hot Tub | Pickle Ball Court
3
3.0
6
Saint Michaels Maryland Private vacation home
From $937 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
5
3.0
10
Easton Maryland Private vacation home
From $1388 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
3
2.0
6
Easton Maryland Private vacation home
From $1003 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock | Golf Cours
6
5.0
12
Easton Maryland Private vacation home
From $2591 per night
(USD)
Downtown St. Michaels Studio – Walk to Waterfront, Dining & Shops
1
1.0
2
Saint Michaels Maryland Apartment
From $372 per night
(USD)
Minutes from Downtown Easton and St. Michaels | Pool | Private Dock
5
3.0
10
Easton Maryland Private vacation home
From $1051 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Kayaks | 350 Ft of Shoreline | Luxur
6
5.0
12
Saint Michaels Maryland Private vacation home
From $1567 per night
(USD)
Downtown Retreat with Bikes, Fire Pit & Kayaks
2
2.0
4
Saint Michaels Maryland Private vacation home
From $582 per night
(USD)
NEWLY Renovated Waterfront Farmhouse in Private Setting!!!
4
3.0
8
Bozman Maryland Private vacation home
From $1049 per night
(USD)
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
2
1.0
4
Tilghman Island Maryland Cottage
From $529 per night
(USD)
Ferry Bridge House
4
4.0
6
Talbot County Maryland Private vacation home
From $858 per night
(USD)
Enjoy the beautiful reflections of sunsets and the golden leaves on the water!
4
3.0
8
Bozman Maryland Private vacation home
From $998 per night
(USD)
Adorable, well-appointed cottage on 2 ac. overlooking beautiful Long Haul Creek
3
2.0
6
St. Michaels Maryland Cottage
From $720 per night
(USD)
Downtown Oxford | Outdoor Dining | Character Filled
3
2.0
6
Oxford Maryland Private vacation home
From $763 per night
(USD)
Waterfront home with private dock near St. Michaels & Easton
4
3.0
8
Easton Maryland Private vacation home
From $1048 per night
(USD)
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
6
4.0
12
St. Michaels Maryland Private vacation home
From $1688 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Hot Tub
2
2.0
4
Bozman Maryland Private vacation home
From $727 per night
(USD)
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
4
2.0
8
Trappe Maryland Private vacation home
From $427 per night
(USD)
Heated pool, sandy beach, pier, and playground set punch point apart!
5
4.0
10
Sherwood Maryland Private vacation home
From $1302 per night
(USD)
Cozy 2BR Home near Idlewild Park
2
1.0
4
Easton Maryland Private vacation home
From $441 per night
(USD)
3-bedroom historic vacation home newly renovated in the middle of Oxford MD.
3
2.0
6
Oxford Maryland Private vacation home
From $174 per night
(USD)
Arcadia Shores on the Cove.
4
4.0
10
Easton Maryland Private vacation home
From $767 per night
(USD)
Minutes from Downtown Cambridge and Downtown Easton | 104+ Acre Farm
4
3.0
8
Trappe Maryland Private vacation home
From $878 per night
(USD)
Saint Michaels Summer Retreat with Pool & Hot Tub
3
3.0
6
Saint Michaels Maryland Private vacation home
From $1022 per night
(USD)
Minutes from Downtown St. Michaels | Pool | Outdoor Kitchen | Private Dock | Hot
5
5.0
10
Easton Maryland Private vacation home
Click For Pricing
Minutes from Downtown St. Michaels | Pool | Cabana | Kayaks | Private Dock
3
3.0
6
St. Michaels Maryland Private vacation home
From $1283 per night
(USD)
Minutes from Downtown St. Michaels | Private Boat Ramp | Dock
3
3.0
6
Bozman Maryland Private vacation home
From $691 per night
(USD)
Travelers Rest Spacious 5BR Pool riverfront Pier charming Easton Saint Michaels
5
3.0
10
Easton Maryland Private vacation home
From $1250 per night
(USD)
Elegant 2-Bedroom Retreat in Historic Saint Michaels – Walk to Dining & Shops
2
1.0
4
Saint Michaels Maryland Apartment
From $694 per night
(USD)
Cozy, Family Friendly, Log Cabin-St. Michaels, MD
4
3.0
8
Saint Michaels Maryland Private vacation home
From $651 per night
(USD)
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