Chesapeake Bay Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Chesapeake Bay

Blufin Bungalows & Marina

Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!

The Anchor ⭐️ 4BR Beach House w Balcony & King Bed

Rooftop Deck Escape! Free Parking!

Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly

Sojourn's Capitol Hill Charmer Superb for Families

Gorgeous 1BR apt/Capitol Hill/Eastern Market Entire rental unit in Washington

Perfect for Families that Want to be Close to DC

3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking.

Your own private beach with this charming 3-bedroom beachfront house!
Holiday Accommodation Chesapeake Bay
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Chesapeake Bay are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Chesapeake Bay itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Chesapeake Bay holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Chesapeake Bay, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Chesapeake Bay with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Chesapeake Bay Holiday Homes essential information
Accommodation | 654 Holiday Homes |
---|---|
Lowest Price | |
Highest Price | |
Popular accommodation | Blufin Bungalows & Marina, Big Waterfront House on the Bay! Amazing Views, Swim Deck, Walk to Beach!, The Anchor ⭐️ 4BR Beach House w Balcony & King Bed, Rooftop Deck Escape! Free Parking!, Arlington Home, Minutes to DC!, Secure Parking, King Bed, Firepit, Pet Friendly, Sojourn's Capitol Hill Charmer Superb for Families, Gorgeous 1BR apt/Capitol Hill/Eastern Market
Entire rental unit in Washington, Perfect for Families that Want to be Close to DC, 3-B rooms 5 beds & 2 BR Spacious House 1 mile from downtown with 2 free parking., Your own private beach with this charming 3-bedroom beachfront house!, The Crows Nest. Sunsets at the Harbor. Enjoy bird’s eye view. Unique location!, Quaint 3/2.5 home in Fort Dupont |
Top cities with Holiday Homes
More Holiday Homes
More accommodations in Chesapeake Bay
Top trending hotels in Chesapeake Bay

Washington Plaza Hotel
More destinations for you
^Eligibility requirements and conditions apply