Vacation Homes in Dorchester County, MD
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top cities with Vacation Homes to explore in Dorchester County

Cambridge
Top Vacation Homes in Dorchester County

Grace Cottage, St Michaels Walk to everything!

Backroad Getaway -New 3-bedroom retreat near Sports at the Beach & DE Turf

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Single family home with screened porch.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Quaint fishing retreat on the lower Potomac Piney Pt

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Top Vacation Homes in Dorchester County

Grace Cottage, St Michaels Walk to everything!

Backroad Getaway -New 3-bedroom retreat near Sports at the Beach & DE Turf

Lovely bay views with kayaks, bikes, fire pit, crabbing & more

3-bedroom house in soothing Saint Leonard with AC for relaxing stays

Single family home with screened porch.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

Quaint fishing retreat on the lower Potomac Piney Pt

Private 2 Acre Waterfront Family Retreat with Pool & Pier

Cottage with Private Water Access | Pet-Friendly | Near St. Michaels

Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels

Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!
Top hotels in Dorchester County

Private 2 Acre Waterfront Family Retreat with Pool & Pier
Find the Best Vacation Homes in Dorchester County
Why book a vacation home in Dorchester County?
Vacation homes in Dorchester County make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Dorchester County?
Private Dorchester County rental homes range between $83 - $304 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Dorchester County vacation home rentals. You might look for Dorchester County rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Dorchester County offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Dorchester County?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Dorchester County. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Dorchester County hotels and vacation homes that best suit your stay. We also have deals for flights, and Dorchester County car rentals. You’ll save even more when you bundle your items into a Dorchester County vacation package!
How many vacation homes are available to book in Dorchester County?
There are 559 rental homes in Dorchester County. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Dorchester County?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Dorchester County Vacation Homes essential information
Accommodation | 559 Vacation Homes |
|---|---|
Lowest Price | $83 |
Highest Price | $304 |
Popular accommodation | Grace Cottage, St Michaels Walk to everything!, Backroad Getaway -New 3-bedroom retreat near Sports at the Beach & DE Turf, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, 3-bedroom house in soothing Saint Leonard with AC for relaxing stays, Single family home with screened porch. , Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Quaint fishing retreat on the lower Potomac Piney Pt, Private 2 Acre Waterfront Family Retreat with Pool & Pier, Cottage with Private Water Access | Pet-Friendly | Near St. Michaels, Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels, Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger! |
Dorchester County Vacation Homes essential information
Accommodation | 559 Vacation Homes |
|---|---|
Lowest Price | $83 |
Highest Price | $304 |
Popular accommodation | Grace Cottage, St Michaels Walk to everything!, Backroad Getaway -New 3-bedroom retreat near Sports at the Beach & DE Turf, Lovely bay views with kayaks, bikes, fire pit, crabbing & more, 3-bedroom house in soothing Saint Leonard with AC for relaxing stays, Single family home with screened porch. , Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly, Quaint fishing retreat on the lower Potomac Piney Pt, Private 2 Acre Waterfront Family Retreat with Pool & Pier, Cottage with Private Water Access | Pet-Friendly | Near St. Michaels, Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels, Secluded, Waterfront Retreat: Fire pit, Private Dock, Game Room, Kayaks!, About Time! - Remote Waterfront Home with Dock - Sleeps 15-New EV Charger! |
Explore More Ways to Travel with Travelocity
- 4 Star Hotels in Cambridge
- 4 Star Hotels in Downtown Cambridge
- Hotels in Algonquin
- Hotels in Annapolis
- Privatevacationhomes in Annapolis
- Agritourism in Anne Arundel County
- Bedandbreakfast in Anne Arundel County
- Cabins in Anne Arundel County
- Hotels near Baltimore Convention Center
- Hotels in Baltimore
- Hotels near Baltimore MD
- Hotels near Bill Burton Fishing Pier State Park
- Hotels near Blackwater National Wildlife Refuge
- Apartments in Cambridge
- Bedandbreakfast in Cambridge
- Cottages in Cambridge
- Aparthotels in Cambridge
- Beach in Cambridge
- Family Friendly in Cambridge
- LGBT Friendly in Cambridge
- Historical in Cambridge
- Balcony in Cambridge
- Free Parking in Cambridge
- Hot Tub in Cambridge
- Waterslide in Cambridge
- Hyatt Regency Chesapeake Bay
- Luxury in Cambridge
- Pet Friendly in Cambridge
- Spa in Cambridge
- Hotels in Cambridge
- Houseboats in Cambridge
- Motels in Cambridge
- Rod 'N' Reel Resort
- Hotels near Choptank River Lighthouse
- Bedandbreakfast in Church Creek
- Cottages in Church Creek
- Motels in Church Creek
- Gaylord National Resort & Convention Center
- Hotels in Deale
- Pet Friendly in Dorchester County
- All-Inclusive in Maryland
- Hot Tub in Maryland
- Maryland Hotels
- Agritourism in Dorchester County
- Cabins in Dorchester County
- Downtown Cambridge Hotels
- Bedandbreakfast in East New Market
- Bedandbreakfast in Eastern Shore
- Cabins in Eastern Shore
- Bedandbreakfast in Easton
- Aparthotels in Easton
- Hotels in Easton
- Houseboats in Easton
- Motels in Easton
- Hotels near Harriet Tubman Museum and Educational Center
- Bedandbreakfast in Hurlock
- Resorts in Hurlock
- Condominiumresort in Maryland
- Inns in Maryland
- Ranches in Maryland
- Ryokans in Maryland
- Hotels near MGM National Harbor Casino
- Hotels near M&T Bank Stadium
- Hotels in National Harbor
- Hotels near Northwest Stadium
- Hotels near Ocean City Boardwalk
- Condos in Ocean City
- Carousel Resort Hotel & Condominiums
- Ashore Oceanfront Hotel by Marriott
- Dunes Suites Oceanfront
- Ocean View in Ocean City
- Princess Royale Oceanfront Resort
- Hotels in Ocean City
- Agritourism in Oxford
- Bedandbreakfast in Oxford
- Inns in Oxford
- Motels in Preston
- Apartments in Royal Oak
- Hotels in Salisbury
- Privatevacationhomes in Secretary
- Bedandbreakfast in St Michaels
- The Wildset
- Hotels in St Michaels
- Bedandbreakfast in Trappe
- Hotels in Trappe
- Motels in Trappe
- Hotels in Waldorf
- Hotels in Washington
- 4 Star Hotels in Cambridge
- 4 Star Hotels in Downtown Cambridge
- Hotels in Algonquin
- Hotels in Annapolis
- Privatevacationhomes in Annapolis
- Agritourism in Anne Arundel County
- Bedandbreakfast in Anne Arundel County
- Cabins in Anne Arundel County
- Hotels near Baltimore Convention Center
- Hotels in Baltimore
- Hotels near Baltimore MD
- Hotels near Bill Burton Fishing Pier State Park
- Hotels near Blackwater National Wildlife Refuge
- Apartments in Cambridge
- Bedandbreakfast in Cambridge
- Cottages in Cambridge
- Aparthotels in Cambridge
- Beach in Cambridge
- Family Friendly in Cambridge
- LGBT Friendly in Cambridge
- Historical in Cambridge
- Balcony in Cambridge
- Free Parking in Cambridge
- Hot Tub in Cambridge
- Waterslide in Cambridge
- Hyatt Regency Chesapeake Bay
- Luxury in Cambridge
- Pet Friendly in Cambridge
- Spa in Cambridge
- Hotels in Cambridge
- Houseboats in Cambridge
- Motels in Cambridge
- Rod 'N' Reel Resort
- Hotels near Choptank River Lighthouse
- Bedandbreakfast in Church Creek
- Cottages in Church Creek
- Motels in Church Creek
- Gaylord National Resort & Convention Center
- Hotels in Deale
- Pet Friendly in Dorchester County
- All-Inclusive in Maryland
- Hot Tub in Maryland
- Maryland Hotels
- Agritourism in Dorchester County
- Cabins in Dorchester County
- Downtown Cambridge Hotels
- Bedandbreakfast in East New Market
- Bedandbreakfast in Eastern Shore
- Cabins in Eastern Shore
- Bedandbreakfast in Easton
- Aparthotels in Easton
- Hotels in Easton
- Houseboats in Easton
- Motels in Easton
- Hotels near Harriet Tubman Museum and Educational Center
- Bedandbreakfast in Hurlock
- Resorts in Hurlock
- Condominiumresort in Maryland
- Inns in Maryland
- Ranches in Maryland
- Ryokans in Maryland
- Hotels near MGM National Harbor Casino
- Hotels near M&T Bank Stadium
- Hotels in National Harbor
- Hotels near Northwest Stadium
- Hotels near Ocean City Boardwalk
- Condos in Ocean City
- Carousel Resort Hotel & Condominiums
- Ashore Oceanfront Hotel by Marriott
- Dunes Suites Oceanfront
- Ocean View in Ocean City
- Princess Royale Oceanfront Resort
- Hotels in Ocean City
- Agritourism in Oxford
- Bedandbreakfast in Oxford
- Inns in Oxford
- Motels in Preston
- Apartments in Royal Oak
- Hotels in Salisbury
- Privatevacationhomes in Secretary
- Bedandbreakfast in St Michaels
- The Wildset
- Hotels in St Michaels
- Bedandbreakfast in Trappe
- Hotels in Trappe
- Motels in Trappe
- Hotels in Waldorf
- Hotels in Washington






