
Hotel holiday rentals near Chesapeake Bay
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Top-rated hotel rentals near Chesapeake Bay
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Classic room #9
Located on the inn's south side, Room 9 offers generous space with a large wardrobe closet, queen-sized bed, and a bathroom set up featuring a step-in tub and shower. Natural light floods the room through its windows, offering a splendid in-room view. Guests staying Monday-Friday are served breakfast at Sugar Water Restaurant from 7-11AM, with a delightful brunch available on Saturdays (10AM-4PM) and Sundays (10AM-2PM). One entree per guest, juice and coffee or tea are included in your stay.

2BR Getaway near Busch Gardens!
Hoping for an unforgettable getaway in Historic Williamsburg? This is it! This charming 2BR-2BA is a luxury to stay in! It offers everything you need for relaxation & adventure. Enjoy on-site recreation, top-notch amenities, and a serene setting with pristine lakes and lush, manicured lawns. After exploring Colonial Williamsburg, 3 miles away, unwind in this picturesque retreat. Plus, Busch Gardens is only 8 miles away, making it the ideal base for experiencing Williamsburg's top attractions!

Modern Cap Hill Suite with Balcony - walk to Metro
Located in the heart of historic Capitol Hill, this beautiful 2 bedroom/1 bathroom apartment with two Queen Beds and a Queen pull out sofa is thoughtfully designed for work and play with incredible walkability to all that DC has to offer. Located just a block away from The Roost Food Hall, where guests can enjoy dining and drinks from local restaurants, or a 10 min stroll to the numerous restaurants and bars of the famous Barracks Row and Eastern Market, you’ll never run out of entertainment.

Meeting House | Queen
Welcome to Meeting House, a distinctive hotel in the little city of Falls Church, Virginia . As a family-owned establishment, we offer personalized service to ensure you will feel right at home throughout your visit. We take pride in offering boutique accommodations, like rental bikes, environmentally friendly toiletries, well-appointed private meeting rooms, and Illy coffee and a house made pastry each morning from Godfrey's, our elegant bakery café. We're excited to have you as our guest!

Suite 5C at Maison Dupont, a Dupont Circle Inn
A former private mansion in the heart of historic Washington, D.C. has been given new life as Maison Dupont, a French inspired boutique hotel (ooh la la!). The hotel is tucked away on a quiet street and is inspired by the fusion of American and French aesthetics which drove much of Washington’s visual history. Visitors will find themselves surrounded by some of the city’s best restaurants, elegant streets, and within walking distance of the White House and a number of world-class museums.

Boutique King Room Near Colonial Williamsburg
Discover the newly renovated Rochambeau Roadside Inn at the gateway to Colonial Williamsburg. Our independent boutique property offers 22 bright, design-forward rooms with vaulted ceilings, woven rugs, vintage furnishings, and local art. The lobby is open limited daytime hours for snacks, drinks, local tips, and complimentary weekend coffee. A perfect mix of nostalgia and comfort just minutes from Colonial Williamsburg and Busch Gardens. Please note our King Rooms are not pet-friendly.

Relax in Style: 3BR Condo w/ Balcony @ Wyndham GG
Welcome to our beautiful 3BR Condo close to Historic Williamsburg! Everything needed for a memorable getaway to historic Williamsburg is right here. Take advantage of on-site recreation and endless amenities in a picturesque setting. The well-manicured lawns and pristine lakes make a lovely retreat after a day of adventuring in Colonial Williamsburg. Just three miles north of historic Williamsburg, we offer easy access to some of Williamsburg's most popular destinations.

Spanish farmhouse vibes at Arrels restaurant
The hotel may require a credit card or deposit for incidentals. Resort fee of USD 40.58 per night, per room is collected by the hotel. Immerse yourself in the energy of the city with our City View King room. This room features a comfortable king-sized bed and offers captivating views of Washington, DC, providing a stylish and relaxing space for your stay. Enjoy the essence of the city from the comfort of your room in our City View King accommodation.

*Historic Powhatan Resort- 4 bedroom sleeps 12
Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

Bright Beach Hideaway
Unwind in this thoughtfully designed Queen room featuring a comfortable queen-size bed and bright, inviting decor. Enjoy modern comforts like a Smart TV, Keurig coffee maker, mini-fridge, microwave, and fast Wi‑Fi. Perfect for solo travelers or couples, it's a relaxing coastal escape just minutes from the Rehoboth Beach boardwalk.

Stylish escape overlooking the Washington Monument
Enjoy exceptional views of the Washington Monument from our 370 sq ft room, featuring two Queen Beds, free Wi-Fi, and a large desk. Relax with handmade bath products, a plush top mattress, bathrobe, and slippers. The room includes a minibar, espresso maker, original artwork, a 55″ HD TV, and a curated micro library.

The Duke Suite at Prince Street Inn
Prince Street Inn is nestled in the heart of Old Town Alexandria, a historic district along the Potomac River marked by cobblestone streets and red brick sidewalks. Located on the quiet side of bustling King Street, stroll through endless indie shops, foodie spots, and open-air eateries by the river.
Popular amenities for hotel rentals near Chesapeake Bay
Family-friendly hotels

You Found it! Spacious Unit, Onsite Pool & Parking

Hotel room 1 street off beach!

Lord Baltimore, 2 Queen Beds

1922 gem on the Nat’l Registry of Historic Places

Room #6 Weightless Lines

Renovated Hotel By Historic Park

One King Room & Sofa Bed Close to APG

Bayfront oasis for every season
Hotels with a pool

Budget-friendly escape on the Boardwalk

Studio with breakfast near APG

Boardwalk location & accessible features

National Harbor Resort 2BR Unit

Suite In Manassas

National Harbor, 1 BR Deluxe

Virginia Beach Resort Timeshare

Studio Suite Kingbed 2@ SBSS Columbia Baltimore
Hotels with a patio

Cozy 3BD Suite in Gorgeous Williamsburg!

Romantic Riverfront Luxury Suite

Williamsburg, VA- Governor's Green-3Bd Dlx

Staybridge Suites DC, Greenbelt

Elite Fireplace Cottage

River Edge Inn

Tysons Corner Suites

Armistead House - Room 101 (First Floor)
Other hotel holiday rentals

Inn Room # 13 - Two double beds

ARC Hotel, Standard 2 Queens

Pet-Friendly Historic Suite Near Baltimore Gems

Upscale Extended Stay Suite Hotel W/Free Breakfast

Boutique Motel in Fairfield

Playfully casual DC home base

Free WiFi and in-room Keurig coffeemaker

Well-appointed home base with Keurig & desk
Quick stats about hotel rentals near Chesapeake Bay

Total holiday rentals
Explore 160 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at € 9 per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
110 properties have a dedicated workspace

Wifi availability
160 of Chesapeake Bay holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals
Destinations to explore
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