Holiday rentals in Chesapeake Bay

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Popular amenities for Chesapeake Bay holiday rentals

Other great holiday rentals in Chesapeake Bay

Guest favourite
Home in Chesapeake
4.98 out of 5 average rating, 61 reviews

Sleeps 6-8, King bed, 2.5 baths

DeborahRating, 5 stars1 week ago
This is my fourth stay at one of Monica's properties and it never disappoints. My visits are consistently pleasant and comfortable. Monica is a great host. I look forward to many returns when visiting my granddaughters in the area.
Top guest favourite
Home in Cape May
5 out of 5 average rating, 17 reviews

Sunset Escape: Cozy Beach House

AlenaRating, 5 stars1 week ago
Nancy is a very nice host! She was always responsive and proactive in providing useful reminders before check-in and check out. Her place is beautiful, new, clean and very cosy. My family loved it and I would book again!
Guest favourite
Apartment in Ocean City
4.96 out of 5 average rating, 23 reviews

Lux Bayfront Unit with Stunning views!

QiaoqiaoRating, 5 stars8 months ago
We had a great time at Steve’s place. The location is amazing - it is walkable and so close to the beach and buzzing shops, while it is so quiet and peaceful indoors. It is clean and cozy, with extraordinary views. We had great breakfasts and enjoyed the beautiful sunset in the balcony. Steve provided detailed instructions proactively, which made the check-in and check-out very smooth. Great place for family vocation.
Superhost
Home in Ocean View
4.83 out of 5 average rating, 23 reviews

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.
Superhost
Home in Pocomoke City
5 out of 5 average rating, 5 reviews

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.
Superhost
Home in Georgetown
4.82 out of 5 average rating, 160 reviews

Maplewood - Simply Comfortable, Dog Friendly

LeahRating, 5 stars1 week 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!
Superhost
Home in Pasadena
4.86 out of 5 average rating, 58 reviews

Beautiful Home Near Beach and Patapsco River

EvaRating, 5 stars4 weeks ago
This home is really nice! We stayed there because our daughter was getting married at a venue about 5 minutes away from the home. It was perfect! Plenty of space for our family and was great for the bridal party to get ready! Nice open floor plan. The beds a bedrooms were very large with comfortable beds. The home was well equipped. The outdoor area was nice and I’m sure the pool is nice in the summertime. Thank you for sharing your home with us on this very special occasion.
Superhost
Townhouse in Williamsburg
5 out of 5 average rating, 8 reviews

4BR/4BA perfect for BIG families! Near attractions

ChrisRating, 5 stars12 months ago
We got a combined two floor apartment (end unit so it was very private) with plenty of space for each of my friends to have their own beds. The back porch and patio were very private and had a beautiful view of the backyard. I would highly recommend this listing!

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