Accommodations in Princess Anne

5 out of 5 average rating, 3 reviews

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

The Cove - 9 Rooms and Conference center

EamonRating, 5 stars21 months ago

Wide open space for our event with a sink, full sized fridge, and mini ice maker. Lots of tables and two bathrooms there as well. 9 hotel style rooms with Jacuzzis, bathrooms, AC, and more. Complimentary gifts and great recommendations along with prompt and helpful responses. My only suggestion is to better sell how good this property is. As of writing this review, the page says there are only 6 beds but there are nine. The pictures of the event area don't properly convey how large and nice it is. Very happy with everything and I'm already trying to find a reason to book this location again next year.

4.99 out of 5 average rating, 151 reviews

Cottage in Frankford

19th Century Coastal Cottage with Modern Amenities

KennethRating, 5 stars1 week ago

Walking into Hobbs and Rose was like entering a welcoming haven…the peace embraced us as we crossed the threshold into the rustic luxury of the cottage. Our favorite snacks and drinks were waiting for us, along with fresh eggs laid by the hens in the quaint chicken house visible from the sunny meditation room. We enjoyed our morning coffee, a special blend ground fresh by the hosts Lisa and Larry, in that same meditation room or sitting in the hammock chairs just feet from the door, an audience to the sometimes animated and sometimes sleeping ducks. We indulged in the offered enhancements of a dinner prepared by Larry, an executive chef and a luxury picnic that lasted us more than two days. The linens were richly comfortable, everything in the cottage was top-of-the-line, and the decor was all lovingly chosen by Lisa. We’re already searching for dates to return to Hobbs and Rose and even though we don’t yet know when we’ll be going back, we can’t wait.

5 out of 5 average rating, 9 reviews

Home in Parsonsburg

M&M Guest House

KathyRating, 5 stars7 months ago

What a lovely, peaceful place! My daughter & I so enjoyed this beautifully appointed cottage. The water, snacks, toiletries were appreciated! The property was quiet; a good location to get to many nearby areas to explore. The only thing we missed was seeing any farm animals & the dog! Marsha was very prompt in responding to questions. We are frequent AirBnB travelers, & this was one of our best experiences. Highly recommend!

4.94 out of 5 average rating, 17 reviews

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

Luxurious & Location 94th st

TiffanyRating, 5 stars7 months ago

This place was perfect for a short bachelorette girl's weekend. It was located in a beautiful spot on the bay. The multiple balconies made it easy to relax and enjoy the views. It was a short walk to a coffee shop that we went to every morning. Easy check in, spotless, and very homey. The decorations and plants made it feel very cozy. I would recommend this place. Short walk to the beach too. Awesome place!

5 out of 5 average rating, 102 reviews

Two Adirondack chairs are positioned beside a wooden dock, shaded by a large umbrella. The view overlooks calm water surrounded by greenery, creating a serene environment. A small table is present between the chairs, enhancing the inviting outdoor seating area.

Cottage in Easton

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

AcaciaRating, 5 stars1 week ago

Cheryl’s stay was so peaceful, comfortable and fun — even before pool season started. We could not believe how large the yard was and how quiet it was. Amazing wildlife. We saw bald eagles, heron, geese and lots of ducks! The house was squeaky clean and had everything we needed. We watched the stars at night and slept soundly. Downtown St. Michael’s is only about 10 minutes away and full of fun things to do. We’re so happy to be acquainted with the area after staying at Cheryl’s!

4.93 out of 5 average rating, 102 reviews

Condo in Rehoboth Beach

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

RalucaRating, 5 stars7 months ago

We had a great time staying at the condo! It was close to the beach, close to local restaurants, very cozy, clean, and Timothy left great suggestions for places to visit and eat at. Checking in and checking out was effortless. Greatly recommend staying with Timothy, and when we come back we hope to get the chance to stay here again!

5 out of 5 average rating, 5 reviews

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

The Old Crab House Bayfront Pool

MichaelRating, 5 stars8 months ago

This was a great location for our family for a Labor Day weekend. We didn't walk to too many places, but everything was very nearby. The main strip was a bit too busy to bike but others were out biking. Parking was accessible. Great location to the beach and not near all the hustle and bustle of the boardwalk. Nice and quiet at night, and the pool was perfect for the kids to hang out in.

Vacation home in Fenwick Island

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.

4.94 out of 5 average rating, 34 reviews

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

MichaelRating, 5 stars7 months ago

Condo has recently been updated and is in excellent condition. Roman was easy to reach and responsive to our questions. East of the Sun is a very nice property. We would consider staying there in the future.

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Get the amount of space that is right for you

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Popular amenities for Princess Anne accommodations

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Princess Anne's top sights

The Washington Inn & Tavern11 locals recommend

Caesar's Pizza Palace6 locals recommend

Teakle Mansion4 locals recommend

Somerset Choice Station4 locals recommend

University of Maryland Eastern Shore4 locals recommend

Spikes Pub & Subs3 locals recommend

Other great vacation rentals in Princess Anne

4.89 out of 5 average rating, 63 reviews

A serene view shows a wooden pathway leading towards the beach at sunrise, with gentle waves visible in the distance. A white chair is positioned on the deck, providing a perfect location to enjoy the peaceful morning scene.

Home in Lusby

Beachfront Oasis with Amazing Views

BrittanyRating, 5 stars1 week ago

Michael's place was perfect for our spring break getaway. I really liked the laid back beach vibe and how kid friendly the house was. The kids were able to walk to beach themselves and had a great time on the trampoline! We loved seeing who could find the most shark teeth.

4.83 out of 5 average rating, 23 reviews

An indoor swimming pool is complemented by a high, wooden-beamed ceiling and large windows that allow natural light to fill the space. The pool is lined with a tiled edge, and seating is available in view of the water.

Home in Ocean View

5 Bedroom-Award Winning Bear Trap Golf Community

VirajRating, 5 stars2 months ago

We had a great time with friends and family over the weekend at your house. it was perfectly sized and spacious. The added advantage of having access to the clubhouse was a perfect arrangement for kids. Sharing a very few things that we think can be improved upon - a. Given the winters are off peak time for this beach town and the fact that outdoor amenities are not usable such as Tennis, Basketball and Pickleball courts, the clubhouse rate is steep. b. Having to carry our own linens is not that big an issue but does add more luggage. at least towels should have been provided. c. None of the toilets had any toiletries. It was clarified before the trip that toiletries will be provided so we were caught off guard. d. The powder room which is the only toilet in the first floor, did not have Trash Can. Otherwise, it was a good outing. There was something to do for everyone. We thoroughly enjoyed. Lynn was generous enough and allowed early check-in.

5 out of 5 average rating, 5 reviews

Home in Pocomoke City

Vacation home near the beaches

NelsonRating, 5 stars9 months ago

Amazing Getaway!! Plenty of indoor and outdoor space, comfortable beds and all around just a wonderful stay. Highly recommend anyone looking for a place to stay with plenty of room and don’t mind a small commute to Chincoteague.

4.82 out of 5 average rating, 160 reviews

A welcoming living area features a stone fireplace and a large television displaying a serene landscape. A wooden dining table is accompanied by black chairs, and natural light is complemented by a stylish chandelier. Comfortable gray seating invites relaxation in this cozy space.

Home in Georgetown

Maplewood - Simply Comfortable, Dog Friendly

LeahRating, 5 stars2 weeks ago

We love coming to Georgetown and love staying at Rick's place. It's perfect for us, and we can relax there. The house is beautiful with great amenities. My mom appreciates the walk-in shower. The kitchen is fantastic for cooking. The beds are comfortable, as is the furniture in living and dining rooms. Rick is a fantastic host. I highly recommend this home!

4.91 out of 5 average rating, 46 reviews

Condo in Ocean City

OCMD family vacation rental 2BR, 2BA, Pool.

RobinRating, 5 stars4 days ago

Absolutely enjoyed our stay at Chris’ place! Very homey feel, close to the things we enjoyed. Felt safe and secure with having our motorcycle with us. This will be my go to from now on! Chris was very quick with his responses to my questions and concerns! Thank you so much for a great and enjoyable stay!!!

4.98 out of 5 average rating, 54 reviews

A bright bedroom features a spacious bed with light linens, complemented by a cozy orange throw. A television is mounted on the wall, and a desk with a chair is positioned near the window, which opens to a private balcony.

Home in Chincoteague

Central Location- Walk to Dining & Entertainment!

BindhuRating, 5 stars1 week ago

We stayed at this house for a short break to visit Chincoteague Island, and it was a wonderful experience. The house was very clean and nicely decorated with a relaxing beach vibe. It had everything we needed for a comfortable stay. The host was incredibly responsive and welcoming, which made us feel right at home. The location is great—close to beautiful beaches, the wildlife refuge, and many good food spots nearby. We would definitely stay here again and highly recommend it to anyone visiting the area.

5 out of 5 average rating, 35 reviews

Home in Selbyville

Stunning Sunrise & Water View 1 mile from Beach

EdRating, 5 stars6 months ago

This was our second time staying at Michael's place and wwe enjoyed everything. The place was clean and spacious and everything was as described. It is a private location but close to Ocean City nightlife and restaurants. You can literally walk to Harpoon Hannah's from the house.