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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Top Cities in Somerset County

A beach with several boats and people fishing.
Holiday RentalsHoliday Rentals

Deal Island

Deal Island

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 AU$350
includes taxes & fees
2 Oct - 3 Oct
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, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is AU$259
includes taxes & fees
27 Sept - 28 Sept
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, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
The price is AU$373
includes taxes & fees
27 Sept - 28 Sept
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, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is AU$453
includes taxes & fees
16 Oct - 17 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, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is AU$348
includes taxes & fees
27 Oct - 28 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, (647 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is AU$323
includes taxes & fees
22 Oct - 23 Oct
Key West Cottages

7. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (330 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is AU$324
includes taxes & fees
13 Oct - 14 Oct
Blufin Bungalows & Marina
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

8. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is AU$487
includes taxes & fees
30 Sept - 1 Oct
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

9. 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 AU$503
includes taxes & fees
19 Oct - 20 Oct
Salisbury Cottage
A single-story house with a front porch, a door, and a mailbox.

10. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is AU$443
includes taxes & fees
27 Sept - 28 Sept
Salisbury Hideaway
A sunroom with wicker furniture, large windows, and a view of the water.

11. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
The price is AU$624
includes taxes & fees
27 Sept - 28 Sept
The purple door at the bay.
A two-story building with a central entrance and a wooden walkway leading to it.

12. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"Beautiful place. I’ve stayed at Assateague Inn on several occasions over the years but this was my first time in 203 and by far the nicest one I’ve stayed in. Newly renovated and tastefully d"
United States
Annette H.
The price is AU$298
includes taxes & fees
28 Sept - 29 Sept
Assateague Inn 203 by Seaside Vacations & Sales
A room with a glass-top coffee table, a white dresser with gold handles, a white door, and a patterned rug.

13. Entire Private Home • Sleeps 6 • Prime Salisbury Location

Entire Private Home • Sleeps 6 • Prime Salisbury Location
Salisbury
10.0 out of 10, Exceptional, (1 review)
"The stay was great. "
United States
Nathaniel N.
The price is AU$456
includes taxes & fees
27 Sept - 28 Sept
Entire Private Home • Sleeps 6 • Prime Salisbury Location
A house with a large lawn and a dock extending into a calm lake.

14. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is AU$467
includes taxes & fees
28 Sept - 29 Sept
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A beachside view with a wooden deck, a chair, and a table.

15. Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (16 reviews)
"Nice pet friendly accommodation. "
United States
Claudia w.
The price is AU$419
includes taxes & fees
2 Oct - 3 Oct
Waterfront Bungalow 2 on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
A sandy beach with footprints and a person walking.

16. 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, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is AU$573
includes taxes & fees
27 Sept - 28 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A covered porch with a red swing chair, white chairs, and a view of the street.

17. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay close to town. Charming screened porch, well appointed kitchen, plenty of space for us."
United States
Veronika B.
The price is AU$708
includes taxes & fees
1 Oct - 2 Oct
The Neigh-Neigh - Location! Location! Location!
A lakeside property with a large house, a shed, and a dense forest in the background.

18. 'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is AU$1,303
includes taxes & fees
27 Sept - 28 Sept
'the Bayside Escape' Remote Chesapeake Bay Estate
A kitchen with a farmhouse sign, a clock, and a refrigerator.

19. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is AU$387
includes taxes & fees
27 Sept - 28 Sept
Cozy Barn Loft: Country Views & Central to Beaches
A staircase with a dark door at the bottom and a light fixture above it.

20. Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
Accomac
10.0 out of 10, Exceptional, (28 reviews)
"Beautiful, comfortable, and quiet. Everything we needed and more!!Very helpful and friendly hosts. "
United States
Karen K.
The price is AU$445
includes taxes & fees
27 Sept - 28 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6
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

Waterside Inn

Waterside Inn

8/10 Good
"have stayed here several times over the years and have always enjoyed our stay. the front desk people are always kind and helpful. the rooms are always clean the beds comfortable, and you have great views from the balcony. the problem is no ramp up to the office so if you have limited mobility such as i that is a major problem. also no rooms have handicap accessible tubs. we do love staying here but as i get older the issues with my mobility may not allow it."
LAWRENCE 3-night trip
Posted 5 hours ago
Waterside Inn

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 favourite 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 depend 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 chosen for you start as low as AU$323 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.