Villa vacation rentals in Delmarva Peninsula

Find and book unique villas on Airbnb

Top-rated villa rentals in Delmarva Peninsula

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

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Guest favorite

Villa in Montross

5.0 out of 5 average rating, 21 reviews

Waterfront+DOCK+Beach+Kayak+Pddlebrd+Arcade

Our serene coastal space with expansive river views is just what you need! Sit back and take in the views, fish, crab or watch the waves and wildlife-dolphins, birds, etc. FEATURES - Water views from nearly every room - Beaches at the end of the street - Dock, fire pit, gas grill, outdoor chairs, arcade console table, cornhole, tennis rackets+pickle ball & more - Kayak, paddle boards & 4 life jackets - 4 crab pots & fishing poles - Clubhouse, pool (summer), tennis courts & more -WiFi & desk

Dec 30 – Jan 6

G$91,263 GYD per night

Guest favorite

Villa in Ocean View

5.0 out of 5 average rating, 11 reviews

Luxury Bethany Beach Villa in Bishop's Landing

Attention Guests - you must be at least 25 years of age or older to book this property. A Community Specific Rental Guest Form Agreement will be emailed and is required to be signed, also to include guest names so to register for pool & shuttle passes. There is refundable $500 security deposit due 36 hours prior to arrival. Failure to agree to these terms will result in denial of your reservation. Please message or contact the host if you have questions about these terms. Enjoy your vacation!

Jun 1 – 8

G$101,640 GYD per night

Guest favorite

Villa in Potomac

5.0 out of 5 average rating, 21 reviews

Hygge, Upscale & Relaxing Luxury

Make memories to last a lifetime in a home that marries luxury with a serene ambiance that embraces the Scandinavian Hygge style, emphasizing a cozy atmosphere and a place to come together and enjoy the company of friends or family. Enchanting and elegant, but far from fussy, our home makes the ideal spot for a family gathering or for a group of friends marking a special occasion. Gather by the fire, play a game of pool, or unwind in the hot tub; there’s something for everyone to enjoy!

Jan 2 – 9

G$143,649 GYD per night

Guest favorite

Villa in Easton

4.95 out of 5 average rating, 38 reviews

St. Michaels Waterfront-Pool/Kayak/Pier/Firepit

Breathtaking views, private pool with baja deck, pier with boat slip, kayaks for 8, 4 bikes, and gas firepit by the water! Great for two families/multi-generations. Two master bedroom suites and great water views from every room. Listing 347588 on vacation rental by owners. Extensive feedback on that site! 7 days during summer. Will consider less please email PETS are $45 per pet per day Must get approval! Pool can be heated at a surcharge. Talbot County license: ST 809 GOL

Sep 14 – 21

G$205,034 GYD per night

Guest favorite

Villa in Hague

4.96 out of 5 average rating, 27 reviews

Sea Glass Paradise

The Seaglass Paradise is an amazing river front property close to Chesapeake Bay. Pets are welcome! Relax on the white sands with family and friends. Fish right off your own private dock, build a fire on the beach at night, and bring your boat ! Boat slips are available to rent at the Marina . Access to the marina pool included in your stay and just a short bike ride away. There is an indoor fireplace for those chillyfalll and winter nights. A Beautiful year round Vacation Home!

Nov 29 – Dec 6

G$75,533 GYD per night

Guest favorite

Villa in Baltimore

5.0 out of 5 average rating, 36 reviews

"The Row Palace" - The Baltimore Sun

This nearly 10,000 sf mansion is located at the heart of Baltimore’s Little Italy (“Piccola Italia”). This is a historic and vibrant community offering cultural festivals throughout the year, a picturesque street scape and authentic bakeries and restaurants featuring multi-region Italian cuisines. This spacious retreat-like Palazzo style mansion is ideal for wedding stays, family gatherings, friend reunions, office retreats, sightseeing, or just celebrating life.

Dec 30 – Jan 6

G$215,465 GYD per night

Superhost

Villa in Sparks Glencoe

4.86 out of 5 average rating, 22 reviews

Stunning 14 Acre Modern Villa with Sunroom

Fully unwind in style at this beautifully renovated two-story modern villa. Nestled in the quiet country of Sparks Glencoe, you'll have ample space to stretch out out and enjoy the numerous luxury amenities surrounding you. From leather furniture, unique lighting fixtures, and marble counters, to a show-stopping spiral staircase and spacious back deck, you'll be forever grateful you didn't opt for a hotel (and its inevitable noisy neighbors).

Feb 11 – 18

G$96,000 GYD per night

Superhost

Villa in Chincoteague

4.93 out of 5 average rating, 15 reviews

Sunset Bay 105-Waterfront POOL & BOAT SlIP

Just Listed! Bayside & Beyond (Sunset Bay Villa #105) is a well appointed 1st floor WATERFRONT condo w/ BOAT SLIP, POOL & GYM in the heart of downtown Chincoteague!!! Walking distance to restaurants, shopping, town park, fishing pier & carnival grounds. Enjoy beautiful sunsets, fishing, crabbing & kayaking from just outside your door! Bayside and Beyond is also within the perfect location to view a rocket launch!

Dec 4 – 11

G$50,546 GYD per night

Superhost

Villa in Princess Anne

4.83 out of 5 average rating, 120 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

Feb 12 – 19

G$207,485 GYD per night

Guest favorite

Villa in Ocean View

4.9 out of 5 average rating, 139 reviews

3 BR 1st floor condo, near beach, resort community

1st FL (no steps),3BR,2BA condo unit 112C, in Village at Bear Trap Dunes resort.Washer/dryer,well-equipped kitchen,deck,screened porch,terrace,4 flat screen TVs,WIFI,DVD player,Netflix,grill,golf,indoor/outdoor pools,tot lots,gym,tennis,saunas,hot tub,restaurant/bar,close to beach,beach shuttle. Great for jogging, walking, biking, rollerblading.

Mar 9 – 16

G$41,735 GYD per night

Guest favorite

Villa in Williamsburg

4.92 out of 5 average rating, 38 reviews

Resort, Studio at Marriott's Manor Club

At Marriott's Manor Club at Ford's Colony, you'll find a historical Williamsburg hideaway that's dedicated to choice, whether you visit renowned theme parks, revisit living history or relax at this beautiful, exclusive retreat. Our Studio (Hotel style guest room) has a comfortable king size bed and a Queen sized sofa.

G$25,734 GYD per night

Guest favorite

Villa in Stevensville

4.87 out of 5 average rating, 38 reviews

Luxurious Waterfront Kent Island Home

Enjoy this beautiful contemporary home in a gated, waterfront community for a perfect weekend getaway! 4 bedrooms, 4 bathrooms, water views, 1 patio with grill and outdoor tables, 2 living spaces (one includes a couch sleeping arrangement) including a billiard table, fooseball table, and more!

Jul 13 – 20

G$105,154 GYD per night