Accommodations in Princess Anne

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Top-rated accommodations in Princess Anne

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

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Superhost

A warm interior space features a brick fireplace as the central focal point. Wooden paneling and a decorative ship's wheel add rustic charm. Natural light floods the area, highlighting the rich wood floors and creating an inviting atmosphere for gatherings.

Hotel room in Crisfield

5 out of 5 average rating, 3 reviews

The Cove - 9 Rooms and Conference center

Breathtaking summer, sunset view from the deck, overlooking Somers Cove Marina and the Little Annemessex River. Relax and enjoy the beauty of a small rustic town. In the heart of Crisfield MD - “The Crab Capital of the World” the Tyler family has owned and operated this property since 1980. This six bed, six bath whole house rental property is great for Family Reunions, Friends Get Together, Small Weddings, Business Meetings, etc. First floor is social area and bedrooms are on the second floor.

Superhost

A modern kitchen area features stainless steel appliances, including a stove, microwave, and refrigerator. Light-colored cabinets provide storage, while a small rug adds comfort to the floor. A separate sleeping area is visible in the background, highlighted by warm tones.

Apartment in Chincoteague

4.5 out of 5 average rating, 6 reviews

Mini Slice of Island Heaven

This special place is close to everything, in the heart of historic downtown. Walk to restaurants, entertainment, and shopping. 10 minute drive to Wildlife Refuge and beach! Our mini slice of heaven is the perfect size for 1 to 2 travelers. Convenience and comfort of a full kitchen, queen size bed, WiFi, TV, full size bathroom, access to laundry on site, and a coffee shop, boutique, and gourmet market on the bottom floor. Local owners excited to host & share the beauty of this amazing island!!

Guest favorite

Cottage in Rehoboth Beach

4.9 out of 5 average rating, 110 reviews

Dog friendly, Close to outlets, fire pit, Sleeps 6

Tucked away in a quiet neighborhood, this adorable cottage awaits your next peaceful vacation. With 3 beds/2 baths, there’s space to enjoy a relaxing stay for up to 6 guests with cozy blankets and beds as well as beautiful surrounding gardens. We are only 4 miles to the beaches, 1 mile to outlet shopping, and close to amazing restaurants. You may not even want to leave the cottage at all. Pet friendly (1 dog please). NEW FOR 2024: beautiful bathroom updates and NEW comfy mattress in the master!

Top guest favorite

A charming cottage is surrounded by lush greenery and vibrant flowerbeds. Exposed brick and dark shutters accentuate the exterior. A welcoming porch features comfortable seating, inviting relaxation amidst the tranquil outdoor setting.

Cottage in Frankford

4.99 out of 5 average rating, 152 reviews

19th Century Coastal Cottage with Modern Amenities

Built from “clinker bricks” in 1941 to house poultry feed, this Airbnb is a dreamy place to slow down. Exposed wood beams and interior brick walls as well as all the luxuries required for a rural escape. This charming cottage near the beach & is surrounded by enchanted gardens. You will swoon over the carved marble bathtub and gorgeous living areas. Perfect for a romantic getaway, Hobbs and Rose Cottage is waiting to create a memorable experience for you! NEW for 2025, our mediation room!

Superhost

A bright living area features a blue sofa and an accent chair, complemented by a light rug. A wall-mounted TV sits on a wooden cabinet, while large sliding doors lead to a balcony with outdoor seating. Natural light enhances the airy ambiance.

Apartment in Rehoboth Beach

4.82 out of 5 average rating, 17 reviews

Penthouse Place

Experience luxury in this newly renovated top-floor condo. White noise machines, plush pillows and mattresses ensure uninterrupted sleep while the cozy screened-in porch offers serene pond views. Relax in plush seating, enjoy modern amenities, and rest easy in comfortable bedrooms. Conveniently located in the highly sought after Creekwood community, it is near dining and entertainment options, this condo offers the perfect blend of luxury and tranquility for your getaway.

Guest favorite

Home in Parsonsburg

5 out of 5 average rating, 9 reviews

M&M Guest House

Relax with the whole family on our 15-acre property. Quiet Cozy Country setting with privacy and nature trails on our property. Only 10 minutes away from Salisbury Md, 30 minutes away from the beaches of Assateague & Ocean city Md. Shopping in Rehoboth, Lewis, Bethany De is an easy 1 hour away. Plenty of things to do such as shopping, beach days, hiking, boating, farmers markets, great eateries in Berlin Md, OC wasabi, Tall Tales Taphouse and plenty more!

Guest favorite

An outdoor seating area is presented with a durable wooden pergola overhead, featuring a comfortable arrangement of light-colored cushions on woven furniture. A coffee table is centered within the seating, and glimpses of nearby buildings and greenery are visible in the background.

Townhouse in Ocean City

4.94 out of 5 average rating, 17 reviews

Luxurious & Location 94th st

This stunning bay view townhouse is the perfect blend of luxury,comfort and relaxation.Step outside to the porch,a perfect spot for outdoor dining,mornings coffee,relaxation or simply enjoying a quiet evening under the stars.This prime location offers within 200-300 ft both a tennis court,basketball court and grocery store.Embrace the coastal lifestyle and experience. This townhouse features two spacious living rooms ideal for cozy family gatherings.

Top guest favorite

A spacious outdoor area features a circular fire pit surrounded by Adirondack chairs on gravel. The cottage stands in the background, complemented by a larger main house. Lush green grass spans the landscape, framed by tall trees and clear blue skies.

Cottage in Easton

5 out of 5 average rating, 102 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

Condo in Rehoboth Beach

4.93 out of 5 average rating, 102 reviews

Cozy condo, 3 pools, and 4 beds in Rehoboth Beach

Get ready to relax immediately in this cozy and bright condo in a quiet community. The condo is a WALK-UP 3rd floor with vaulted ceilings, multiple balconies, and a relaxing screened porch with a view. We provide linens for the beds, bath towels, boogie boards, and beach chairs. Just over a mile from the beach and within walking distance are 3 community pools, a brewery, a grocery store, seafood restaurants, a water park, and more.

Superhost

A wooden deck leads down to a gravel path surrounded by lush greenery. Two red chairs are positioned on the gravel area, enjoying the serene view of the woods. Soft landscape lighting is present along the path, enhancing the natural surroundings.

Tiny home in Salisbury

4.83 out of 5 average rating, 127 reviews

Cattail's Branch

Enjoy the lovely setting of this romantic spot in nature. Tiny house sits on Widow Hawkins Branch Creek and backs up to Johnson Wildlife Mtg Area. Great for bird watchers and nature lovers. Enjoy sitting by the fire pit or relaxing on spacious deck overlooking creek. Quiet and peaceful. Fully equipped kitchen, Queen bed, bathroom, pull out queen sofa bed with privacy wall to make 2rd bedroom. Close to beaches and town.

Superhost

An outdoor seating area features two woven chairs and a coffee table, arranged on a striped rug. Brightly colored pillows in orange and turquoise provide a pop of color against the neutral tones of the patio. Nearby, large windows allow natural light to enter the interior.

Home in Ocean City

5 out of 5 average rating, 5 reviews

The Old Crab House Bayfront Pool

Welcome to The Old Crab House! Nestled along the tranquil bayside, our newly remodeled 1 bedroom condo exudes sophistication with high-end finishes and decor. Enjoy luxurious living with modern amenities, including a sparkling pool. Discover seaside serenity and upscale comfort in every detail of this stunning retreat. Walking distance to the beach restaurants and nightlife. Book your stay today!

Guest favorite

An outdoor resort-style pool is surrounded by concrete decking, with several lounge chairs positioned for relaxation. Nearby, lush greenery and flowering shrubs contribute to the inviting atmosphere. The clear blue sky reflects above the water, enhancing the tranquil setting.

Vacation home in Fenwick Island

4.94 out of 5 average rating, 34 reviews

Cozy, updated condo. Pool, tennis, walk to beach.

NEW KITCHEN COMING FOR 2025! Updated 2 bedroom condo in quiet beautifully maintained community, with screened in porch overlooking zen-like garden. Quick walk to beach, plus a resort style pool and tennis court. New furniture, beds, carpet and paint. Refreshed kitchen and baths, and super clean!