Montgomery Cottages - Vacation Rentals in Chesapeake
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Luxury Places to Stay in Chesapeake
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Top-Rated Vacation Rentals with a Pool in Chesapeake
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Pet-Friendly Vacation Rentals in Chesapeake
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Large Vacation Homes & Villas in Chesapeake
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Wheelchair Accessible Vacation Homes in Chesapeake
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Chesapeake Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Chesapeake
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About Chesapeake Vacation Rentals
With more than 72 Chesapeake 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.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Montgomerycottages Chesapeake, 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. Places to stay near Chesapeake are 628.8 ft² on average, with prices averaging US $209 a night.
Montgomerycottages makes it easy and safe to find and compare vacation rentals in Chesapeake 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
| Type | Count |
|---|---|
| Vacation Homes | 29 |
| Holiday Apartments | 22 |
| Hotels | 18 |
| B&B | 1 |
| Cabin Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Chesapeake
★ 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.
Weather in Chesapeake
View the weather forecast for Chesapeake before booking your Chesapeake Vacation Rentals to confirm your best time to go.
Top Attractions Around Chesapeake, OH
Montgomerycottages offers a large selection of top attractions around Chesapeake. Research things to do on your vacation before you visit Chesapeake.
Chesapeake Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Chesapeake?
There are a lot of options in Chesapeake. If you plan on staying in the Chesapeake 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:
- Cozy 2-bedroom apartment located next to St. Mary's Hospital!
- The Park House A 5 Bedroom Retreat w/Game Room & Fire Pit
- Chessie Room
- The Blue House – Eclectic Art Haven Near Marshall & Huntington’s Best Parks
- Nucor Welcome! Peaceful and Private Ranch
- Huntington Modern - Mins to DT, MU, St. Mary's
- Exceptionally clean, safe, private side by side duplex 3 minutes to stadium
- Updated 2BR home in Huntington, WV
- The West Virginia Penthouse
- Cozy & Modern 1-Bedroom Downstairs Apartment with King Bed + Queen Sofa Bed
How many vacation rentals have private pools in Chesapeake?
There are 1 vacation rentals with private pools near Chesapeake. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Chesapeake are best for families?
If you are looking for a family-friendly vacation home in Chesapeake, 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:
How many vacation rentals are available in Chesapeake?
Currently, the total number of properties listed in 2026 is over 72 in the Chesapeake area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Chesapeake.
