Vacation rentals in Somerset County

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Top-rated vacation rentals in Somerset County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Crisfield

5.0 out of 5 average rating, 66 reviews

Marshall’s Retreat Chesapeake small town getaway

Modern 3 bedroom home centrally located in the heart of Crisfield, Md. Off & on street parking. Minutes away from our towns new bike trail, boat & Kayak launch, parks, Wellington Beach, shopping, Ferry’s to The Islands, fishing piers, restaurants, Crab & Cruise, 413 crab & concert, beautiful views. about an hour drive to Ocean City, Assateague or Chincoteague. Or stay in & relax watch Cable tv, Wifi. Please be sure to research the area online to make sure it’s right for your needs. Thanks

Dec 24 – 31

$124 per night

Guest favorite

Cottage in Westover

4.99 out of 5 average rating, 179 reviews

Rumbley Cottage on the Tangier Sound-Private Beach

Winter time is a great time at Rumbley! Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all window. Look out to the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Wifi, Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Feb 24 – Mar 3

$295 per night

Guest favorite

Home in Deal Island Historic District

5.0 out of 5 average rating, 12 reviews

House of the Setting Sun/Deal Island Bayfront Home

Soak up the quiet beauty of Tangier Sound at this bayfront getaway with stunning sunset views among the pines. Enjoy crabbing, fishing, and swimming off the dock. Dive into nature photography, birdwatching, hunting, kayaking in the wetlands, and more. There's a small local beach less than 5 minutes away. It's far enough away to unplug, but less than an hour to Ocean City, Chincoteague, and Assateague. And there's plenty to enjoy onsite, including sunsets 9 months out of the year!

Jan 9 – 16

$186 per night

Guest favorite

Home in Crisfield

4.95 out of 5 average rating, 254 reviews

Cozy Home near Waterfront in Crisfield, MD

Our home is close to great views, restaurants and shopping, the beach and family-friendly activities. You’ll love the sunsets over the water and viewing working boats in the harbor. Great for couples, solo adventurers, business travelers, and families (with kids). Beach is walking distance and the boat launch is 1/2 mile away. New library, playground, fishing, crabbing and gorgeous sunsets are all close by. Owners live only 15 minutes away for anything you may need.

Sep 25 – Oct 2

$140 per night

Guest favorite

Home in Crisfield

5.0 out of 5 average rating, 17 reviews

Myrtle Manor- Crisfield Maryland

Welcome to our newly renovated Pearl Certified home located in beautiful downtown Crisfield Maryland! Whether you want to explore our small town on the new bike trail, shop the small businesses in town, visit Janes Island State Park, relax on Wellington Beach, take a day trip to Smith Island, or enjoy an evening Sunset Cruise on the bay - the choices are unlimited. Or you may just want to relax and enjoy our home which has cable TV and WIFI.

Jun 2 – 9

$132 per night

Guest favorite

Cottage in Westover

4.92 out of 5 average rating, 142 reviews

Heaven on the Bay - A Peaceful Waterfront Retreat

This Chesapeake Bayfront cottage has spectacular views to take you away from everything in any season. It boasts more than 120 feet of waterfront, and you can dangle your feet off the 70 ft “dock of the bay”. Launch kayaks from the small sandy beach in summer, or cozy up to the wood stove in the winter. Inside, you’ll find wood floors throughout, modern kitchen & baths with bay views from every room. Kayaks, SUP, bicycles & crab traps too!

Oct 31 – Nov 7

$203 per night

Guest favorite

Cottage in Saxis

4.87 out of 5 average rating, 204 reviews

ISLAND SUNSETS Near Chincoteague Island

1 - Story build early 1950’s Near Chincoteague Island Virginia Assateague Beach NASA Wallops Island, Va. Onancock, Va Waterman’s Fishing Village Surrounded by Water on three sides & Virginia Wildlife Refuge on fourth side. 400 ft. Walking distance to Beach, Kayaking & Canoeing, Wildlife, Fishing Pier, Boat Ramp, Marina, Public Pavilion, Ice Cream Shop, 2 Restaurants, Museum, Multiple Seafood Shantys

Aug 10 – 17

$169 per night

Superhost

Villa in Princess Anne

4.83 out of 5 average rating, 119 reviews

Waterfront Retreat & Guest House

Enjoy a relaxing private retreat with an amazing view of the water. Come to stay at the house the whole time enjoying sunsets, kayaking, building sand castles, playing in the water, and making great meals or venture to many nearby towns with great restaurants, hikes, golfing, breweries, bike paths, and more. Enjoy your own private 100 ft pier and sandy beach. **great wifi in main house and guesthouse

Sep 6 – 13

$788 per night

Guest favorite

Cottage in Smith Island

5.0 out of 5 average rating, 37 reviews

IDLEHOUR, 3 BEDROOMS 2 BATHS W/ DOCK

Unwind and relax after a busy life in the city. Get comfortable and enjoy plenty of extra room at this spacious place. Awake refreshed and ready for a day of kayaking, bicycling and or exploring the island. We have a deep water dock (4 houses down from the house) for crabbing, launch the kayaks, boat mooring or just relaxing. A large hot & cold outdoor shower for that nature experience.

Dec 23 – 30

$158 per night

Guest favorite

Guest suite in Deal Island Historic District

4.91 out of 5 average rating, 88 reviews

Private guest suite near Deal Island Maryland

Nothing extraordinary here. What I have available, at a reasonable rate is a clean private suite. With self check-in using kwikset smart code touchpad electronic deadbolt. Private driveway with plenty of room for your truck and boat. Room and deck are handicap accessible using entry ramp or steps.

Feb 18 – 25

$60 per night

Guest favorite

Cottage in Deal Island Historic District

4.96 out of 5 average rating, 68 reviews

Private Beachfront Cottage with 2 Bedrooms + Loft

Relax and enjoy your own private beach with panoramic views of the Chesapeake Bay! Our cottage is in a quiet strip of Deal Island shoreline, but still boasts high speed internet - so you don't have to completely disconnect while you're here ...unless you want to, of course. We won't tell.

May 7 – 14

$237 per night

Guest favorite

Home in TYLERTON

4.95 out of 5 average rating, 118 reviews

3 bedroom/2.5 bath Smith Island bungalow with dock

The Quietness of the island and the beautiful scenery around the waters edge. You will hear the birds and the waves and the wind. The island is void of loud noises, mostly nature. The home was built around 1860 and fully restored 2008. its perfectly imperfect!

Mar 23 – 30

$132 per night