Holiday Homes in Chesapeake Bay

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (167)
"excellent place to stay on the water"
Blufin Bungalows & Marina

Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger

10.0 out of 10, Exceptional, (13)
"Beautiful location . Close to all the things. Very convenient.. Felt like home!"
The price is AU$497
includes taxes & fees
24 Aug - 25 Aug
Private top floor at 2067 Park Road, Nw Dc. P.sCheck out 2nd listing too- bigger

The Art Door only minutes from beach

9.8 out of 10, Exceptional, (89)
"Loved the stay! Property was very clean, quiet and easy to get to everything Virginia Beach has to offer. The property manager was very quick to respond and helpful. Will stay there again"
The price is AU$361
includes taxes & fees
26 Aug - 27 Aug
The Art Door only minutes from beach

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is AU$291
includes taxes & fees
2 Sept - 3 Sept
Cottage near the Bay

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (39)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AU$472
includes taxes & fees
27 Aug - 28 Aug
Relax on Kent Island in 3 Bedroom Home w/Waterview

3br/2ba Waterfront Home overlooks Private Dock. 2+ acres of front yard Games

10.0 out of 10, Exceptional, (25)
"We had a great time fishing, kayaking, paddle boarding and checking out the area! Definitely a great place for a family to stay. "
The price is AU$878
includes taxes & fees
24 Aug - 25 Aug
3br/2ba Waterfront Home overlooks Private Dock. 2+ acres of front yard Games

Historic charm with modern amenities

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is AU$571
includes taxes & fees
31 Aug - 1 Sept
Historic charm with modern amenities

Cozy Barn Loft: Country Views & Central to Beaches

10.0 out of 10, Exceptional, (18)
"Loft was spotless, and had everything we needed. "
The price is AU$418
includes taxes & fees
24 Aug - 25 Aug
Cozy Barn Loft: Country Views & Central to Beaches

Tranquil 3BR/2.5ba house with 4 beds for 7/Patio/BBQ & Gaming Room/15 mins to DC

2.0 star property
9.4 out of 10, Exceptional, (20)
"Overall a very nice stay."
The price is AU$781
includes taxes & fees
25 Aug - 26 Aug
Tranquil 3BR/2.5ba house with 4 beds for 7/Patio/BBQ & Gaming Room/15 mins to DC

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (53)
"The roundhouse was amazing on many levels, figuratively and literally. There are many creature, comforts throughout this sprawling home and the views were serene and relaxing, and the couches and beds were comfy! And the host was very helpful and accommodating. Highly recommend would definitely stay here again."
The price is AU$844
includes taxes & fees
1 Sept - 2 Sept
Stunning waterfront panoramic view getaway house

Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

10.0 out of 10, Exceptional, (26)
"Wonderful stay and beautiful accomodations"
The price is AU$493
includes taxes & fees
2 Sept - 3 Sept
Newly Constructed Second Floor Modern Studio Apartment Unit 2 ~ Sleeps 6

Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.

9.6 out of 10, Exceptional, (38)
"Loved yorktown, loved the neighborhood, and had a great time. "
The price is AU$351
includes taxes & fees
17 Sept - 18 Sept
Yorktown - 3 private rooms and bath for 1 group/party. Not a whole home rental.

Private Apt 1 Bedroom Hi-Speed Internet, DC Metro.

9.8 out of 10, Exceptional, (36)
"Close to everything and on a bus line. Clean and very pleasant."
The price is AU$339
includes taxes & fees
26 Aug - 27 Aug
Private Apt 1 Bedroom Hi-Speed Internet, DC Metro.

Beautiful 2 Bedroom with Loft in Heart of Old Town—sleeps 6

9.8 out of 10, Exceptional, (48)
"Great Location! Really cool town."
The price is AU$593
includes taxes & fees
25 Aug - 26 Aug
Beautiful 2 Bedroom with Loft in Heart of Old Town—sleeps 6

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is AU$709
includes taxes & fees
24 Aug - 25 Aug
The purple door at the bay.

Waterfront Hotel Suite with Balcony

8.0 out of 10, Very good, (1)
"Overall, I enjoyed my stay. I love the fact that the restaurant was walking distance. They had an outside bar, pool and room’s balcony was just a peaceful environment. I did not like that the cottage community patio trash was overflowing and my room was super dusty. You could tell sweeping/swiffer was not done and a previous person‘s shoes were found under the bed."
The price is AU$391
includes taxes & fees
5 Sept - 6 Sept
Waterfront Hotel Suite with Balcony

Sojourn | Coastal Cottage | 3 BR

9.4 out of 10, Exceptional, (31)
"We stayed here for an extended weekend and it was such a cute place! Very clean and relaxing. The beach is just a couple minutes of walking from the house and easy to get to. "
The price is AU$759
includes taxes & fees
4 Sept - 5 Sept
Sojourn | Coastal Cottage | 3 BR

Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

9.0 out of 10, Wonderful, (35)
"Property is as listed. Very clean, comfortable and had everything we needed for our trip. "
The price is AU$575
includes taxes & fees
23 Sept - 24 Sept
Modern Oasis- Downtown Luxury Stay, Spacious Cozy Home

Hidden Fells Point Gem / Private Courtyard Patio

9.6 out of 10, Exceptional, (87)
"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."
The price is AU$318
includes taxes & fees
25 Aug - 26 Aug
Hidden Fells Point Gem / Private Courtyard Patio

Sojourn Aviators Dream on Back River

9.6 out of 10, Exceptional, (25)
"My family enjoyed the experience of staying near the water. The views were lovely! "
The price is AU$686
includes taxes & fees
16 Sept - 17 Sept
Sojourn Aviators Dream on Back River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesapeake Bay Hotel Reviews