
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.

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

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.

Near Potomac Mills | Indoor Pool + On‑Site Dining
Enjoy a modern, convenient stay at Courtyard Potomac Mills Woodbridge, ideally located just off I-95 and minutes from Potomac Mills Outlet Mall. Perfect for business, weekend getaways, or family trips, the hotel offers newly updated rooms with plush bedding, HDTVs, and workspaces, plus great amenities like an indoor pool, restaurant, and 24-hour fitness center. Only 25 miles south of Washington, D.C., you’ll be close to shopping, dining, and top regional attractions.

Near Reagan National Airport + Dining & Shuttle
Stay steps from Washington, D.C. at AC Hotel Arlington National Landing, where modern European-inspired design meets urban comfort. Enjoy craft cocktails and tapas at AC Kitchen & Lounge, energize in the fitness center, or unwind in stylish rooms with sleek décor and premium bedding. Perfectly positioned near the National Mall, The Pentagon, and Reagan National Airport, this stay connects you effortlessly to Arlington’s dining, history, and D.C.’s top attractions.

Beach Bum Inn Bayview room with balcony
Not a cookie- cutter hotel room experience- enjoy a clean, simple room just steps away from the beach and the Boardwalk. Small indoor plunge pool. Featuring private balconies facing bayside with unforgettable sunsets, mini fridge, microwave, and hair dryer in each guest room. Sit your beach chairs right outside your door. Light continental breakfast included for each registered guest. Kick back and relax... you're on beach time!

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.

Elegant DC Escape | European Breakfast & Lounge
Welcome to AC Hotel Washington DC Convention Center, your stylish home base in the heart of D.C. Relax in sleek, modern rooms designed for comfort, enjoy delightful European-inspired breakfasts, or unwind with craft cocktails at AC Lounge. Stay energized at our 24-hour fitness center. Steps from museums, landmarks, dining, and events at Capital One Arena, it's the perfect spot for your memorable capital city adventure.

Guest room, 1 King in Washington, DC
Steps from Union Station and Capitol Hill, Washington Marriott Capitol Hill blends elevated design with unbeatable location in DC’s vibrant NoMa district. Explore Smithsonian museums (under 1.5 miles), the National Mall, and top dining spots. Enjoy on-site favorites like the Ciel rooftop lounge, Society Commons, and a massive fitness center with an outdoor HIIT yard—all in a pet-friendly, amenity-rich stay. ✨

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.

Beachside Queen Haven
Enjoy comfortable seaside living in this spacious Double Queen room, featuring two plush queen-size beds perfect for families or friends. Modern conveniences like a Smart TV, mini-fridge, microwave, Keurig coffee maker, and complimentary Wi‑Fi ensure a relaxed and stylish stay. Located just steps from Rehoboth Beach, this bright coastal retreat blends home-like comfort with beachside convenience.

Brand New Modern 3BR | Stylish, Comfortable
Stylish, Comfortable & Fully Equipped Enjoy a stay in this brand-new 3-bedroom apartment designed for comfort, style, and convenience. Perfect for families, couples, or business travelers, the space features modern finishes, comfortable furnishings, and everything you need for a relaxing stay. The apartment includes a fully equipped kitchen, three bedrooms with TVs, and a clean modern bathroom.

Coastal Studio King
This charming Studio King offers a plush king bed and modern coastal décor, ideal for couples or solo travelers seeking comfort by the sea. With a cozy seating area, flat-screen TV, mini-fridge, and complimentary Wi‑Fi, it combines style and convenience seamlessly. Just steps away from the courtyard, pool, and vibrant Rehoboth Beach dining and shopping scene, it's your perfect seaside escape.
Popular amenities for hotel rentals near Chesapeake Bay
Family-friendly hotels

Easy access to DC & just 10 mins from the airport

Iconic Bethesda Stay | Zoo. Fitness Center

Classic Room #7

Arlo Washington Dc

Near Washington, D.C. | Breakfast. Bar. Wi-Fi.

Walk to U.S. Capitol | Rooftop Bar. Gym + Dining

Journey At The Capitol | Air & Space Museum. Pool

Historical Sites | Capitol Hill. Outdoor patio
Hotels with a pool

Scenic Stay | Sightseeing. Free Breakfast!

You Found it! Spacious Unit, Onsite Pool & Parking

HoJo Ocean City | King + Sofa | Walk to Boardwalk

Relax in Style: 3BR Condo w/ Balcony @ Wyndham GG

Steps to Metro | Free Breakfast. Indoor Pool + Gym

Easily walkable to the ocean, shops & more

Quick DC Access + Indoor Pool + Restaurant On-Site

*Greensprings Resort- 4 bedrooms sleeps 12
Hotels with a patio

Studio with breakfast near APG

Two Queen Beds Near Aberdeen Proving Ground

guesthouse by good neighbor | room 103

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

2BR Getaway near Busch Gardens!

Colonial Style 1BR at Kingsgate

1 BR at Old Town Alexandria

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

The Quincy, an Ascend Collection Hotel

Hotel room 1 street off beach!

Club Quarters Hotel White House, Washington Dc

Prime Location in Washington DC| Free Breakfast!

Unwind poolside, or paddle across the bay

Lord Baltimore, 2 Queen Beds

Governor Calvert King | Historic Inns

Playfully casual DC home base
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 £45 per night before taxes and fees

Verified guest reviews
Over 1,420 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
40 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
- Rentals with pools Chesapeake Bay
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