
Hotel holiday rentals near Chesapeake Bay
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Top-rated hotel rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

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 breakfast. A perfect mix of nostalgia and comfort just minutes from Colonial Williamsburg and Busch Gardens. Please note our King Rooms are not pet-friendly.

Comfy King Bed | Free Breakfast. Free Parking
avid hotel Richmond North - Ashland, an IHG Hotel, is located in Glen Allen, just minutes from Kings Dominion Amusement Park and Virginia Commonwealth University. With easy access to I-95 and I-295, it's ideal for exploring attractions like the State Capitol, Richmond Coliseum, and Richmond International Raceway. Business travelers will appreciate proximity to major companies and Richmond International Airport, 30 km away. ✔ Free breakfast ✔ Indoor pool ✔ Pet-friendly ✔ Free parking

Quick DC Access + Indoor Pool + Restaurant On-Site
Make Ballston your easy D.C. base at this Hotel in Arlington, perfectly located steps from the Metro, local dining, and all the fun spots around town. Surrounded by trendy cafés, rooftop bars, and boutique shops, this modern retreat puts you minutes from Washington D.C.’s top landmarks. After exploring, float in the heated indoor pool, fit in a quick workout at the fitness studio, or unwind with bites and cocktails on site, all in one of Arlington’s most walkable and vibrant neighborhoods.

Historic Charlesworth Hotel On The Delaware Bay
The Charlesworth Hotel and Restaurant is a hidden gem located in Fortescue, NJ. We are on the water and boast some of the best sunsets in the world. The original hotel was built in 1924. We have 4 quaint rooms altogether along with a coffee lounge area. Our guest enjoy the view of the bay, sunbathing, sea glass and driftwood hunting, fishing, crabbing, ect. This place is a perfect getaway. Please note each room has to be rented has to separately. Room 1 private bathroom.

Minutes from Washington, D.C. | Dining. Fitness.
Start your East Coast journey in comfort and style at Hyatt Centric Arlington Adults Only Hotel, just minutes from Washington, D.C. Perfect for business travelers and vacationers, our hotel offers a variety of dining options, including breakfast packages. Hyatt Centric Arlington is located less than 200 feet from the Rosslyn Metro Station, which allows you to access charming neighborhoods like Foggy Bottom and Georgetown within minutes.

Walk to Navy Yard | Rooftop Bar. Restaurant & Gym
Stay steps from the U.S. Capitol and Navy Yard at AC Hotel Washington DC Capitol Hill. Enjoy rooftop views at Smoke & Mirrors Bar, modern rooms with Smart HDTVs and free Wi-Fi, and European-inspired breakfast at AC Kitchen. Walk to Nationals Park or explore nearby Smithsonian museums via Metro. On-site perks include a fitness center, 2 restaurants, curated retail, hydration stations, and sleek guest rooms designed for productivity.

Walk to Smithsonian | Indoor Pool & On-site Dining
Stay just two blocks from the White House at Hilton Garden Inn Washington DC Downtown. With McPherson Square Metro across the street, you’re minutes from the Smithsonian Museums, the National Mall, and Capitol Hill. Reach DCA Airport in about 17 minutes by metro. Enjoy easy access to the Convention Center, Capital One Arena, and Lincoln Memorial, all within two miles, plus an on-site restaurant, fitness center, and indoor pool.

Near Wolf Trap National Park + Breakfast. Pool.
Spread out, sleep in, and sip free cocktails at this two-room suite stay near Tysons Corner. Wake up to made-to-order breakfast (hello, omelets), hop on the Metro to explore D.C., or chill by the indoor pool after a day of shopping or sightseeing. With on-site parking, and a separate living room in every suite, it’s the perfect mix of hotel perks and homey space—no tiny rooms or shared kitchens here.

Bayfront oasis for every season
Our rooms offer lots of air space with 9-foot-high ceilings, setting the stage for a no-limits stay. Sleep easy at our hotel with ultra-comfortable, Aloft signature beds. Our fast and free Wi-Fi gives you the bandwidth you need to work easy and play hard. Try our signature coffee blends and free water in all our hotel rooms in Ocean City, Maryland.

King Suite | SpringHill Suites | Historic Triangle
Settle into a refreshed Williamsburg stay with the space and convenience of an all-suite hotel. Plan a day at Jamestown, Yorktown, or family favorites like Water Country USA. With a kitchenette and complimentary on-site parking, you’ll have a comfortable hub for shopping at the Premium Outlets, The Pottery, and local Virginia tasting rooms.

Dog friendly room with 2 double beds
Standard room with 2 double beds at Beach Bum Inn on 3rd street & Baltimore Ave. Just 1 block to the beach and the Boardwalk. This room is located on the 1st floor and allows DOGS (no other pets) for a $75 fee (up to 2). Short walk to the 3rd st dog friendly bayside park and playground. Small indoor pool. Grab-n-go breakfast.

The Duke Suite and 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

2 Queen Beds | Free Parking. Free Breakfast. Pool

Steps to Dupont Circle + Rooftop Pool. Bar. Dining

Steps to Nationals Park + Bistro, Pool & Gym

Iconic Landmarks | Georgetown Waterfront. Pool

Near Reagan National Airport + Dining & Shuttle

Easy access to DC & just 10 mins from the airport

Beachfront high-rise with stunning views

*Kingsgate - One Bedroom
Hotels with a pool

Relax in Style: 1BR Condo w/ Balcony at Wyndham GG

Near Reagan Airport | City Views. Sushi Bar + Pool

National Harbor Resort 2 Bedroom Unit Downtown

Kingsgate Resort- 1 bedroom

Escape To Our Beachfront Oasis | Private Beach

*Steps to Metro| Free Breakfast. Indoor Pool + Gym

Close to White House + Rooftop Terrace. Pool. Gym.

You Found it! Spacious Unit, Onsite Pool & Parking
Hotels with a patio

Meeting House | Double Full

guesthouse by good neighbor | room 103

Armistead House - Room 101 (First Floor)

Gorgeous Studio at Patriots' Place

Deluxe 1BD in Governor's Green

Colonial Style 1BR at Kingsgate

2 BD Condo at Governor's Green!

One Bedroom at the Amazing Oceanaire Resort!
Other hotel holiday rentals

Playfully casual DC home base

The Quincy, an Ascend Collection Hotel, Selecte...

Governor Calvert King | Historic Inns

Cricket Hill House — Waterfront Suite, 3 North

Prime Location in Washington DC| Free Breakfast!

Walk to Bethesda Metro Station + Restaurant & Gym

Romantic Retreat | Pet Friendly | Parking Onsite

Hotel room 1 street off beach!
Quick stats about hotel rentals near Chesapeake Bay

Total holiday rentals
Explore 200 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 1,610 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 140 rentals that welcome pets

Holiday rentals with a pool
80 properties feature pools

Rentals with dedicated workspaces
140 properties have a dedicated workspace

Wifi availability
200 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
- Beach house rentals Chesapeake Bay
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- Hotel rooms United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Nauticus
- Town Point Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall




