Coffee Hawaii - Vacation Rentals in Chesapeake

The Park House A 5 Bedroom Retreat w/Game Room & Fire Pit From US $383
         

Chessie Room From US $171
         

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10.0 (20 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • View
Fairfield Inn & Suites by Marriott Huntington From US $121
         

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9.2 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Updated 2BR home in Huntington, WV From US $167
         

10.0 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Huntington Modern - Mins to DT, MU, St. Mary's From US $330
         

Luxury Places to Stay in Chesapeake

Over 63+ Luxury Places to Stay in or Near Chesapeake
The West Virginia Penthouse From US $701
         

10.0 (6 Reviews)
Apartment
  • Air Conditioner
  • Wheelchair Accessible
  • Accessibility
Cozy With A Little Touch of Love From US $451
         

7.8 (6 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Walk to Ritter Park: Renovated Home Near Marshall! From US $260
         

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8.5 (2 Reviews)
House
  • Parking
  • Security/Safety
  • Fireplace/Heating
Walk to Marshall University: Home w/Private Yard! From US $216
         

Monthly Stay Special! Cozy Cottage in Huntington From US $204
         

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10.0 (1 Review)
House
  • Parking
  • Security/Safety
  • Sports/Activities

Top-Rated Vacation Rentals with a Pool in Chesapeake

Over 17+ Top-Rated Vacation Rentals with a Pool in or Near Chesapeake
Cozy 1-bedroom, Pool & Hot Tub Access From US $90
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pool
Fairfield Inn & Suites by Marriott Huntington From US $122
         

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9.0 (410 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Delta Hotels by Marriott Huntington Downtown From US $140
         

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9.0 (204 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Delta Hotels by Marriott Huntington Downtown From US $146
         

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8.8 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Huntington University Area From US $120
         

8.8 (887 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
TownePlace Suites by Marriott Huntington From US $141
         

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8.6 (321 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn University Area, Huntington, Wv From US $97
         

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8.5 (223 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
DoubleTree by Hilton Huntington From US $114
         

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8.4 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Chesapeake

Over 15+ Pet-Friendly Vacation Rentals in or Near Chesapeake
Cosy single-level home with laundry and parking From US $75
         

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7.1 (10 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Top-Floor Duplex Near Marshall University From US $147
         

Nucor Welcome! Peaceful and Private Ranch From US $156
         

10.0 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Highly Rated for Cleanliness, quiet/cozy space near St Mary's From US $114
         

Large Vacation Homes & Villas in Chesapeake

Over 3+ Large Vacation Homes & Villas in or Near Chesapeake
Beautiful Two Story with In ground Pool From US $600
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Econo Lodge Huntington - Barboursville University Area From US $143
         

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6.7 (259 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • Accessibility

Wheelchair Accessible Vacation Homes in Chesapeake

Over 6+ Wheelchair Accessible Vacation Homes in or Near Chesapeake
TownePlace Suites Huntington From US $134
         

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8.3 (80 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Suites South Point - Huntington From US $95
         

8.2 (609 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
DoubleTree by Hilton Huntington, WV From US $114
         

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7.9 (359 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn Huntington University Area From US $101
         

7.6 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Quality Inn Huntington University Area From US $94
         

7.0 (288 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Comfort Inn Huntington near University area From US $114
         

7.6 (845 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Chesapeake Vacation Rentals and Airbnb Places to Stay Under $200

Over 27+ Chesapeake Vacation Rentals and Airbnb Places to Stay Under $200
Urban Cottage: Homey & Convenient From US $127
         

9.4 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • View
Econo Lodge Huntington - Barboursville University Area From US $140
         

7.6 (369 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area
Urban Cottage:Homey & Convenient From US $176
         

9.8 (23 Reviews)
House
  • TV
  • Security/Safety
  • Fireplace/Heating
Exposed Brick by Uni,Arena,Hosp+Towel Warmer,Robes From US $154
         

Cozy 1-bedroom apartment in tranquil Huntington with AC From US $145
         

New
Apartment
  • Air Conditioner
  • Designated Smoking Area
  • Bedding/Linens

Instantly Bookable Vacation Homes in Chesapeake

Over 6+ Instantly Bookable Vacation Homes in or Near Chesapeake
Spacious 2BR-1 Block from downtown From US $90
         

10.0 (1 Review)
House
  • Security/Safety
  • Child Friendly
Aparthotel- Green Goddess by Arena/Univ/Hospital From US $102
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Cute little stone house on the hill From US $177
         

9.6 (19 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Blue House on the Hill close to it all From US $115
         

8.6 (7 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Designated Smoking Area
Full House - Safe and Great Location From US $179
         

5.0 (6 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Bedding/Linens

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, Coffeeshawaii 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 Coffeeshawaii 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 617.27 ft² on average, with prices averaging US $169 a night.

Coffeeshawaii 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 21
Hotels 18
B&B 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Chesapeake

Pro Tip: Coffeeshawaii makes it easy to compare the best listings on Coffeeshawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Coffeeshawaii 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.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Chesapeake, OH


Chesapeake Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Chesapeake?
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:

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.