Compare Chesapeake Bay Condo Rentals

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Featured Chesapeake Bay Condo Rentals

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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.

Chesapeake Bay Accommodation Oceanfront

    Inn at Huntingfield Creek

    Inn at Huntingfield Creek

    4928 Eastern Neck Rd, Rock Hall, MD
    $156 nightly
    The price is $173 total per night from Nov 2 to Nov 3
    $173 total
    Nov 2 - Nov 3
    Total with taxes and fees
    10/10 Exceptional! (54 reviews)
    Comfort Suites Chincoteague Island Bayfront Resort

    Comfort Suites Chincoteague Island Bayfront Resort

    4195 Main St, Chincoteague, VA
    $114 nightly
    The price is $129 total per night from Oct 26 to Oct 27
    $129 total
    Oct 26 - Oct 27
    Total with taxes and fees
    9.6/10 Exceptional! (1,013 reviews)
    Inn at Perry Cabin

    Inn at Perry Cabin

    308 Watkins Ln, St. Michaels, MD
    $549 nightly
    The price is $604 total per night from Nov 3 to Nov 4
    $604 total
    Nov 3 - Nov 4
    Total with taxes and fees
    9.4/10 Exceptional! (364 reviews)
    Annapolis Waterfront Hotel, Autograph Collection

    Annapolis Waterfront Hotel, Autograph Collection

    80 Compromise St, Annapolis, MD
    $212 nightly
    The price is $241 total per night from Nov 2 to Nov 3
    $241 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.8/10 Excellent! (868 reviews)
    Hilton Garden Inn Kent Island Marina

    Hilton Garden Inn Kent Island Marina

    3206 Main St, Grasonville, MD
    $147 nightly
    The price is $163 total per night from Oct 26 to Oct 27
    $163 total
    Oct 26 - Oct 27
    Total with taxes and fees
    8.8/10 Excellent! (998 reviews)
    Anchor Inn

    Anchor Inn

    3791 South Main Street, Chincoteague, VA
    $76 nightly
    The price is $85 total per night from Oct 31 to Nov 1
    $85 total
    Oct 31 - Nov 1
    Total with taxes and fees
    8.8/10 Excellent! (554 reviews)
    Hyatt Regency Chesapeake Bay

    Hyatt Regency Chesapeake Bay

    100 Heron Blvd, Cambridge, MD
    $233 nightly
    The price is $265 total per night from Oct 6 to Oct 7
    $265 total
    Oct 6 - Oct 7
    Total with taxes and fees
    8.6/10 Excellent! (1,012 reviews)
    Best Western Plus Holiday Sands Inn & Suites

    Best Western Plus Holiday Sands Inn & Suites

    1330 E Ocean View Ave, Norfolk, VA
    $80 nightly
    The price is $95 total per night from Nov 2 to Nov 3
    $95 total
    Nov 2 - Nov 3
    Total with taxes and fees
    7.8/10 Good! (1,029 reviews)
    Americas Best Value Inn Princess Anne

    Americas Best Value Inn Princess Anne

    30359 Mt. Vernon Road, Princess Anne, MD
    $70 nightly
    The price is $77 total per night from Oct 5 to Oct 6
    $77 total
    Oct 5 - Oct 6
    Total with taxes and fees
    6.4/10 (51 reviews)

Hotel Options in Chesapeake Bay

    Washington Plaza Hotel

    Washington Plaza Hotel

    10 Thomas Circle NW, Washington, DC
    $109 nightly
    The price is $126 total per night from Oct 5 to Oct 6
    $126 total
    Oct 5 - Oct 6
    Total with taxes and fees
    8.6/10 Excellent! (4,667 reviews)
    Hamilton Hotel Washington DC

    Hamilton Hotel Washington DC

    1001 14th St NW, Washington, DC
    $166 nightly
    The price is $188 total per night from Oct 31 to Nov 1
    $188 total
    Oct 31 - Nov 1
    Total with taxes and fees
    8.6/10 Excellent! (2,824 reviews)
    citizenM Washington DC Capitol

    citizenM Washington DC Capitol

    550 School St SW, Washington, DC
    $129 nightly
    The price is $150 total per night from Oct 31 to Nov 1
    $150 total
    Oct 31 - Nov 1
    Total with taxes and fees
    8.8/10 Excellent! (2,828 reviews)

Luxury Condos

Find luxury condos in Chesapeake Bay
Get your vacation off to a fabulous start by booking a luxury condo in Chesapeake Bay. They’re a great option if you want to pamper yourself a little more than usual on your next getaway. Plus, they give you a unique opportunity to see the city the way a local would. You’re not in a hotel—you’re home. Condominiums come in all shapes and sizes, and with Orbitz on your side, you’ll find exactly the right one for your trip.

Stay in a Chesapeake Bay condo
Vacation condo rentals are a nice alternative to hotels with perks such as multiple bedrooms, living rooms, balconies, laundry facilities, Wi-Fi access and espresso machines. And don’t underestimate the power of the full kitchen in your condo: whipping up midnight snacks is a breeze, and hey, making a meal on your own without worrying about ordering in or going out to eat is just plain convenient. You might also have a pool, a gym and a hot tub on the property or close by.  

Exploring Chesapeake Bay will be a breeze with a downtown condo as your home base. You’ll be close to the top sights, and within walking distance of great restaurants, shopping, and bars. Got leftovers? Put them in your fridge. Remember, you’re living like a local now.

Chesapeake Bay Condo Rentals essential information

Accommodation
71 Condo Rentals
Lowest Price
$77
Highest Price
$604
Popular accommodation
Kingsmill water-view studio, minutes to Busch Gardens & Colonial Williamsburg!, Perfectly located minutes from the Inner Harbor, Ravens and Orioles stadium., "Pura Vida" Fabulous 4 Bed Home near H St & Union Market, Water-view in Kingsmill, 10 minutes to Busch Gardens & Colonial Williamsburg!, Kingsmill Condo on Golf Course 9th Fairway! Local owner, Waterfront on Marsh Island!, Luxury Riverfront Condo w/ sunrise & sunset views, Only 5 min to Assateague National Seashore!, Downtown Loft & Close to EVERYTHING!

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