
Places to stay near Chesapeake Bay
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Top-rated vacation rentals near Chesapeake Bay
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Condo rentals with wifi

The Bird's Nest in Historic Occoquan (Mins to DC)

Oceanfront Gem VaB Studio Exceptional Views

Cozy Oxford Getaway

Casa 1776 - Spacious Apartment | Heart of Downtown

Hill East BnB - Modern Style and Comfort 3BR/3BA

Lux in heart of DC social scene, free parking!

Newly Renovated 1BR Condo Sleeps 2 - Unit 1

Modern 2 bed 2 bath unit in hip DC neighborhood
Family-friendly house rentals

Osprey's roost: Spring and summer 2025

Cove Point Beach Cabin

Newly Renovated Modern 3 bed 2 bath Water Front

Cozy Riverside Cottage in the Woods

"Queen Bee “ WATERVIEW & WALK TO ACCESS the River

3 bedroom/2.5 bath Smith Island bungalow with dock

Top of the Chesapeake - Private Waterfront Home

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa
Apartment rentals with air conditioning

Our Little Piece of Heaven

The Fish House

Stunning Sunsets on Breton Bay, Seaside apartment

Private cozy cottage - center of Chestertown .

Historic St. Mary's City, MD

Serenity Suite on Chesapeake Bay

Beach Highway Hobby Farm

Romantic Wtrfrnt Flat+Solarium@Chesapeake Paradise
Other great vacation rentals near Chesapeake Bay

Nice Guest Suite at Chesapeake Bay

Relaxing Water Views - Mill Creek Cottage

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

A "True" Chesapeake Bay Waterfront Experience!

Beach Please! River cottage w/private beach & dock

TooFine Lakehouse, pet friendly waterfront cottage

Peaceful Waterfront 3 BR/2BA

Sunkissed Cottage-private, natural waterfront home
Quick stats about vacation rentals near Chesapeake Bay
Total rentals
6.9K properties
Total number of reviews
272K reviews
Family-friendly rentals
4.6K properties are a good fit for families
Pet-friendly rentals
2.7K properties allow pets
Rentals with a pool
840 properties have a pool
Rentals with dedicated workspaces
3.8K properties have a dedicated workspace
Destinations to explore
- Cabin rentals Chesapeake Bay
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- Family-friendly rentals Chesapeake Bay
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- Virginia Beach Oceanfront
- Resort Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Buckroe Beach and Park
- Grandview Beach
- Assateague Beach
- Kingsmill Resort
- Outlook Beach
- Haven Beach
- Jamestown Settlement
- Ocean Breeze Waterpark
- Sarah Constant Beach Park
- Norfolk Botanical Garden
- Kiptopeke Beach
- Wilkins Beach
- Wallops Beach
- Piney Point Beach
- Golden Horseshoe Golf Club
- Little Creek Beach
- Chrysler Museum of Art
- Cape Charles Beachfront
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