Montgomery Cottages - Vacation Rentals in Chesapeake Bay
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![Award Winning Ocean Front Architectural Gem [Home Share per VA Beach Zoning]](https://imgservice.montgomerycottages.com/640x370/award-winning-oce-us-virginia-beach-ha-321391482-0.jpg)
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Luxury Places to Stay in Chesapeake Bay
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Top-Rated Vacation Rentals with a Pool in Chesapeake Bay
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Pet-Friendly Vacation Rentals in Chesapeake Bay
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Large Vacation Homes & Villas in Chesapeake Bay
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Wheelchair Accessible Vacation Homes in Chesapeake Bay
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Chesapeake Bay Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Chesapeake Bay
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About Chesapeake Bay Vacation Rentals
With more than 28103 Chesapeake Bay vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Montgomerycottages and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Chesapeake Bay.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Chesapeake Bay, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Chesapeake Bay. Places to stay near Chesapeake Bay are 734.35 ft² on average, with prices averaging US $364 a night.
Montgomerycottages makes it easy and safe to find and compare vacation rentals in Chesapeake Bay with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Chesapeake Bay
| Type | Count |
|---|---|
| Vacation Homes | 11849 |
| Holiday Apartments | 7763 |
| Hotels | 3442 |
| Resorts | 758 |
| Cottages | 628 |
| B&B | 437 |
| Villas | 290 |
| Cabin Rentals | 94 |
| Others | 63 |
| Hostels | 19 |
| Ski Chalet Rentals | 5 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake Bay
★ Pro Tip: Montgomerycottages makes it easy to compare the best listings on Montgomerycottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Montgomerycottages homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Chesapeake Bay.
Weather in Chesapeake Bay
View the weather forecast for Chesapeake Bay before booking your Chesapeake Bay Vacation Rentals to confirm your best time to go.
Top Attractions Around Chesapeake Bay, US
Montgomerycottages offers a large selection of top attractions around Chesapeake Bay. Research things to do on your vacation before you visit Chesapeake Bay.
Other Places to Stay Near Chesapeake Bay, US
Complexes around Chesapeake Bay, US
Chesapeake Bay Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chesapeake Bay?
There are a lot of options in Chesapeake Bay. If you plan on staying in the Chesapeake Bay area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Chesapeake Bay:
- Cottage on a Private Island in the York River
- Cozy, Dog-friendly Duplex At The North End Short Walk To The Beach!
- Adorable Cottage In The Heart Of The Old Beach Area, Close To The Boardwalk.
- Captivating Chesapeake experience
- Historic Cottage on Ware River Estate
- Breezy, Quaint, and Dog- Friendly North End duplex.
- Riverfront House, Dock, Hot Tub, Salt Pool, near beach, Free WiFi
- PET-FRIENDLY! Just Steps To Famous Chincoteague Pony Penning & Carnival Grounds
- Private 2,000 Sq Ft Cottage in Historic Yorktown- w/trolley access
- PERFECT LOCATION in the heart of history
How many vacation rentals have private pools in Chesapeake Bay?
There are 1344 vacation rentals with private pools near Chesapeake Bay. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chesapeake Bay are best for families?
If you are looking for a family-friendly vacation home in Chesapeake Bay, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Chesapeake Bay:
How many vacation rentals are available in Chesapeake Bay?
Currently, the total number of properties listed in 2026 is over 28103 in the Chesapeake Bay area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake Bay.
