A waterfront with a pier extending into the water, a building labeled 'Ice Cream Gallery', and a boat docked nearby.

Somerset County Holiday Rentals

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Our top choices for Somerset County holiday rentals

A sandy beach with footprints, a pier in the distance, and a clear sky.

1. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is NZ$418
includes taxes & fees
3 Nov - 4 Nov
Tangier Escape, great place get away from it all on Deal Island, MD.
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

2. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
The price is NZ$327
includes taxes & fees
26 Oct - 27 Oct
Cottage near the Bay
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

3. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is NZ$447
includes taxes & fees
26 Oct - 27 Oct
Deal Island Bay Cottage
A marina at sunset with boats docked and buildings in the background.

4. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is NZ$577
includes taxes & fees
26 Oct - 27 Oct
Come out and enjoy Autumn at the HH Ranch on Smith Island.
A room with a large bed, multiple windows, and a ceiling fan.

5. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (28 reviews)
"I loved the location, the cleanliness and how good I felt being there. Thank you"
United States
Carmen
The price is NZ$441
includes taxes & fees
28 Oct - 29 Oct
Salisbury Riverfront Lofts
A waterfront house with a balcony, dock, and a view of the water.

6. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (665 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is NZ$378
includes taxes & fees
25 Nov - 26 Nov
Key West Cottages
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

7. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is NZ$325
includes taxes & fees
8 Nov - 9 Nov
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A single-story house with a front porch, a door, and a mailbox.

8. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is NZ$608
includes taxes & fees
26 Oct - 27 Oct
Salisbury Hideaway
A bedroom with a bed, bedside tables, a lamp, and a painting on the wall.

9. Newly updated 3 bedroom cottage with Solo Stove fire pit

Newly updated 3 bedroom cottage with Solo Stove fire pit
Reedville
9.6 out of 10, Exceptional, (28 reviews)
"I always stay here when I come for work it’s a pretty nice place quiet and clean I highly recommend it to everyone it’s visiting"
United States
Luis A.
The price is NZ$446
includes taxes & fees
26 Oct - 27 Oct
Newly updated 3 bedroom cottage with Solo Stove fire pit
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

10. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is NZ$606
includes taxes & fees
27 Oct - 28 Oct
Salisbury Cottage
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

11. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (72 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is NZ$725
includes taxes & fees
26 Oct - 27 Oct
Bayfront Modern Retreat • Dock, Kayaks, Views
A sandy beach with footprints and a person walking.

12. Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (49 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is NZ$717
includes taxes & fees
17 Nov - 18 Nov
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

13. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is NZ$351
includes taxes & fees
26 Oct - 27 Oct
Assateageue Inn 104 by Seaside Vacations & Sales
A cozy living room with a dining area, featuring a ceiling fan, a sofa, a coffee table, and a bookshelf.

14. Misty Mare Townhouse - Gorgeous home on Chincoteague Island

Misty Mare Townhouse - Gorgeous home on Chincoteague Island
Snotty Ridge
9.8 out of 10, Exceptional, (19 reviews)
"Great location, easy check in, very clean, well decorated"
United States
sue g.
The price is NZ$569
includes taxes & fees
26 Oct - 27 Oct
Misty Mare Townhouse - Gorgeous home on Chincoteague Island
A sunroom with wicker furniture, large windows, and a view of the water.

15. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (69 reviews)
"Great location"
United States
Rick K.
The price is NZ$803
includes taxes & fees
3 Nov - 4 Nov
The purple door at the bay.
A cozy living room with a sofa, a coffee table, and a TV mounted on the wall.

16. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (7 reviews)
"Ramsey is a great host and provided everything we needed!"
United States
Kendall M.
The price is NZ$528
includes taxes & fees
26 Oct - 27 Oct
Cozy 2-bedroom house in Chincoteague
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

17. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
Retro Hipster: Close to downtown, dining and fun
An open doorway leading to a living room with a fireplace, a dining area, and a kitchen visible through an open door.

18. Deluxe corner apartment with riverfront views close to dining and downtown

Deluxe corner apartment with riverfront views close to dining and downtown
Salisbury
8.8 out of 10, Excellent, (6 reviews)
"Lovely apartment in the heart of Salisbury. Ckean, well appointed, and comfortable. "
United States
Gretel S.
The price is NZ$420
includes taxes & fees
26 Oct - 27 Oct
Deluxe corner apartment with riverfront views close to dining and downtown
A two-story building with a central entrance and a wooden walkway leading to it.

19. Assateague Inn 204 by Seaside Vacations & Sales

Assateague Inn 204 by Seaside Vacations & Sales
Chincoteague Island
7.4 out of 10, Good, (3 reviews)
"We had short trip for the oyster festival but really enjoyed our stay. It was quiet and cozy. Beautiful views off the deck. "
United States
Jen E.
The price is NZ$365
includes taxes & fees
24 Nov - 25 Nov
Assateague Inn 204 by Seaside Vacations & Sales
A modern kitchen with wooden ceiling, white cabinets, stainless steel appliances, and a central island with seating.

20. Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
3.0 star property
Tangier
The price is NZ$646
includes taxes & fees
26 Oct - 27 Oct
Unique Tangier Cottage w/ Chesapeake Bay Views!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Somerset County Hotel Reviews

Key West Cottages

Key West Cottages

10/10 Excellent
"Property was in pristine condition when we arrived. Cottage was easily accessible from the parking lot and the luggage wagons are a life saver ! Would definitely recommend this place. Staff is so helpful and super kind. We will definitely be back."
Ursula 3-night trip
Posted 9 hours ago
Key West Cottages

Find out more about Somerset County

Everything you need to know about Somerset County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Somerset County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Somerset County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Somerset County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Somerset County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Somerset County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Somerset County holiday rentals we have selected for you start as low as NZ$327 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Somerset County rentals

At Expedia, we put the best Somerset County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Somerset County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Somerset County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Somerset County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.