Best Chesapeake Vacation Rentals
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Top location
Econo Lodge Chesapeake Route 13 And I-464
- Continental breakfast
- 24-hour reception
- Leisure/ TV room
- Hair dryer
- Golf centre
- Golf course
Econo Lodge Chesapeake Route 13 And I-464 is located approximately 7 km from Children's Museum of Virginia and provides business guests with a fax service. Offering Wi-Fi, the property is located around 10 minutes by car from Oak Grove Lake Park.
Econo Lodge Chesapeake Route 13 And I-464
- Continental breakfast
- 24-hour reception
- Leisure/ TV room
- Hair dryer
- Golf centre
- Golf course
Econo Lodge Chesapeake Route 13 And I-464
Econo Lodge Chesapeake Route 13 And I-464 is located approximately 7 km from Children's Museum of Virginia and provides business guests with a fax service. Offering Wi-Fi, the property is located around 10 minutes by car from Oak Grove Lake Park.
Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Flat-screen TV
- Ironing facilities
- Terrace
Located about 10 minutes by car from West Side Christian Church, the 4-bedroom Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home provides access to various tourist attractions in the vicinity. With a maximum capacity of 8 guests, the property offers a private parking lot.
Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Flat-screen TV
- Ironing facilities
- Terrace
Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home
Located about 10 minutes by car from West Side Christian Church, the 4-bedroom Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home provides access to various tourist attractions in the vicinity. With a maximum capacity of 8 guests, the property offers a private parking lot.
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Beach access
Spacious Chesapeake Home W/ Pool Table!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Ironing facilities
- Spa & wellness centre
Positioned a 19-minute walk from bustling shopping destinations such as Chesapeake Square Mall, the welcoming Spacious Chesapeake Home W/ Pool Table! offers guests to use a private parking lot.
Spacious Chesapeake Home W/ Pool Table!
- Cookware/ Kitchen utensils
- Free parking
- 24-hour reception
- Ironing facilities
- Spa & wellness centre
Spacious Chesapeake Home W/ Pool Table!
Positioned a 19-minute walk from bustling shopping destinations such as Chesapeake Square Mall, the welcoming Spacious Chesapeake Home W/ Pool Table! offers guests to use a private parking lot.
Cheap Chesapeake Vacation Rentals
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Great deal
Bright Chesapeake Home Near Shopping & Dining
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Terrace
Bright Chesapeake Home Near Shopping & Dining is located 4.5 km from COGASOC- Temple Beth El, giving access to various tourist spots nearby. With a maximum capacity of 4 guests, this 2-bedroom welcoming holiday home offers parking.
Bright Chesapeake Home Near Shopping & Dining
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Terrace
Bright Chesapeake Home Near Shopping & Dining
Bright Chesapeake Home Near Shopping & Dining is located 4.5 km from COGASOC- Temple Beth El, giving access to various tourist spots nearby. With a maximum capacity of 4 guests, this 2-bedroom welcoming holiday home offers parking.
Beautiful Home In Chesapeake
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Garden area
Offering access to entertainment venues such as Cinema Cafe, situated approximately 25 minutes' walk away, the 3-bedroom Beautiful Home In Chesapeake can host up to 7 guests.
Beautiful Home In Chesapeake
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Garden area
Beautiful Home In Chesapeake
Offering access to entertainment venues such as Cinema Cafe, situated approximately 25 minutes' walk away, the 3-bedroom Beautiful Home In Chesapeake can host up to 7 guests.
Prime Location In Chesapeake With Spacious 4Br & Big Kitchen
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
The 4-bedroom Prime Location In Chesapeake With Spacious 4Br & Big Kitchen villa is located approximately 25 minutes' walk from Chesapeake Conference Center, giving access to various tourist spots nearby. This Chesapeake holiday home is suitable for up to 11 guests and features parking.
Prime Location In Chesapeake With Spacious 4Br & Big Kitchen
- BBQ facilities
- Free parking
- Air conditioning
- Flat-screen TV
- Ironing facilities
- Terrace
Prime Location In Chesapeake With Spacious 4Br & Big Kitchen
The 4-bedroom Prime Location In Chesapeake With Spacious 4Br & Big Kitchen villa is located approximately 25 minutes' walk from Chesapeake Conference Center, giving access to various tourist spots nearby. This Chesapeake holiday home is suitable for up to 11 guests and features parking.
Pet Friendly Vacation Rentals Chesapeake Virginia
Landing - Modern Apartment With Amazing Amenities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Fitness centre
The 1-bedroom Landing - Modern Apartment With Amazing Amenities Chesapeake is located in Chesapeake, around 25 minutes' walk from Deep Creek United Methodist Church, and offers guests a swimming pool and a fitness suite. Deep Creek City Park is 4.5 km from this 72 m² apartment in Chesapeake.
Take advantage of fitness classes at the accommodation to elevate your leisure experience.
Landing - Modern Apartment With Amazing Amenities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Fitness centre
Landing - Modern Apartment With Amazing Amenities
The 1-bedroom Landing - Modern Apartment With Amazing Amenities Chesapeake is located in Chesapeake, around 25 minutes' walk from Deep Creek United Methodist Church, and offers guests a swimming pool and a fitness suite. Deep Creek City Park is 4.5 km from this 72 m² apartment in Chesapeake.
Take advantage of fitness classes at the accommodation to elevate your leisure experience.
Landing Modern Apartment With Amazing Amenities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Fitness centre
The spacious 1-bedroom Landing Modern Apartment With Amazing Amenities Chesapeake features a prime location about 25 minutes' walk from Deep Creek United Methodist Church and hosts up to 2 guests. Also, the presence of a swimming pool guarantees a relaxing stay.
Maintain your exercise routine effortlessly at a fitness club offered by the accommodation.
Landing Modern Apartment With Amazing Amenities
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Fitness centre
Landing Modern Apartment With Amazing Amenities
The spacious 1-bedroom Landing Modern Apartment With Amazing Amenities Chesapeake features a prime location about 25 minutes' walk from Deep Creek United Methodist Church and hosts up to 2 guests. Also, the presence of a swimming pool guarantees a relaxing stay.
Maintain your exercise routine effortlessly at a fitness club offered by the accommodation.
National At The Helix
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Fitness centre
- Outdoor swimming pool
The 56 m² National At The Helix Apartment Chesapeake features a convenient location 25 minutes' walk from Oak Grove Lake Park and hosts up to 2 guests. Wi-Fi and a charging station for electric vehicles are also available at the apartment.
You can take advantage of a fitness studio, so it’s easy to keep up with your exercise routine.
National At The Helix
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Fitness centre
- Outdoor swimming pool
National At The Helix
The 56 m² National At The Helix Apartment Chesapeake features a convenient location 25 minutes' walk from Oak Grove Lake Park and hosts up to 2 guests. Wi-Fi and a charging station for electric vehicles are also available at the apartment.
You can take advantage of a fitness studio, so it’s easy to keep up with your exercise routine.
Chesapeake Vacation Rentals Oceanfront
Evergreen House 1
- Free parking
- Air conditioning
- Flat-screen TV
The spacious Evergreen House 1 Chesapeake is located 25 minutes' walk from the art Portlock Galleries at SoNo and offers Wi-Fi for either business or leisure.
Evergreen House 1
- Free parking
- Air conditioning
- Flat-screen TV
Evergreen House 1
The spacious Evergreen House 1 Chesapeake is located 25 minutes' walk from the art Portlock Galleries at SoNo and offers Wi-Fi for either business or leisure.
Nyakio Suite
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
The 102 m² Nyakio Suite Chesapeake is located 10 minutes by car from the art Portlock Galleries at SoNo and 3.8 km from Chesapeake City Park. Wi-Fi and parking are also available at this 2-bedroom apartment.
A seasonal outdoor swimming pool can be found on the premises.
Nyakio Suite
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Outdoor swimming pool
Nyakio Suite
The 102 m² Nyakio Suite Chesapeake is located 10 minutes by car from the art Portlock Galleries at SoNo and 3.8 km from Chesapeake City Park. Wi-Fi and parking are also available at this 2-bedroom apartment.
A seasonal outdoor swimming pool can be found on the premises.
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Best-rated
Dances Bay
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Saltwater pool
Dances Bay Apartment Elizabeth City is located in Elizabeth City, a 10-minute drive from Symonds Creek Tabernacle, and boasts a hot tub. Wi-Fi and a car park are provided for guests' utmost comfort.
The perfect getaway includes access to a sundeck and a picnic area, allowing guests to experience the pinnacle of relaxation. A range of activities, such as canyoning and fisheries are offered in the area.
Dances Bay
- Shared kitchen
- Free parking
- Air conditioning
- Flat-screen TV
- Jacuzzi
- Saltwater pool
Dances Bay
Dances Bay Apartment Elizabeth City is located in Elizabeth City, a 10-minute drive from Symonds Creek Tabernacle, and boasts a hot tub. Wi-Fi and a car park are provided for guests' utmost comfort.
The perfect getaway includes access to a sundeck and a picnic area, allowing guests to experience the pinnacle of relaxation. A range of activities, such as canyoning and fisheries are offered in the area.
Chesapeake Vacation Rentals with Private Pool
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Guest favorite
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Beach access
Beach Luxury Oceanfront
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Outdoor swimming pool
To enjoy your vacation in Virginia Beach, stay at the 2-room Beach Luxury Oceanfront Virginia Beach apartment, which is only 500 metres from First Baptist Church and merely a 9-minute stroll from King Neptune Statue on the Boardwalk. Wi-Fi and a car park are also available at the apartment.
An outdoor swimming pool can be found at the property.
Beach Luxury Oceanfront
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Outdoor swimming pool
Beach Luxury Oceanfront
To enjoy your vacation in Virginia Beach, stay at the 2-room Beach Luxury Oceanfront Virginia Beach apartment, which is only 500 metres from First Baptist Church and merely a 9-minute stroll from King Neptune Statue on the Boardwalk. Wi-Fi and a car park are also available at the apartment.
An outdoor swimming pool can be found at the property.
Downtown Norfolk Loft
- Cookware/ Kitchen utensils
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Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Located merely 6 minutes' stroll from the Iowa-class battleship "USS Wisconsin BB-64", the spacious 98 m² Downtown Norfolk Loft Apartment accommodates up to 2 guests. Enjoying a convenient setting, the 1-bedroom apartment lies 3.5 km from the 53 - acre Virginia Zoological Park and just moments from NAUTICUS The National Maritime Center.
Downtown Norfolk Loft
- Cookware/ Kitchen utensils
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Car park
Charges may apply
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
Downtown Norfolk Loft
Located merely 6 minutes' stroll from the Iowa-class battleship "USS Wisconsin BB-64", the spacious 98 m² Downtown Norfolk Loft Apartment accommodates up to 2 guests. Enjoying a convenient setting, the 1-bedroom apartment lies 3.5 km from the 53 - acre Virginia Zoological Park and just moments from NAUTICUS The National Maritime Center.
Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Sun terrace
Situated approximately 4 km from the historically black Hampton University, the 5-bedroom Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues Hampton offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Providing guests with Wi-Fi and a private parking lot, the holiday home is about 10 minutes' drive from the riverfront Gosnold's Hope Park.
Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues
- Cookware/ Kitchen utensils
- Free parking
- VIP check-in/ -out
- Air conditioning
- Golf centre
- Sun terrace
Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues
Situated approximately 4 km from the historically black Hampton University, the 5-bedroom Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues Hampton offers guests to enjoy a sunbathing terrace, a picnic area, and a golf course. Providing guests with Wi-Fi and a private parking lot, the holiday home is about 10 minutes' drive from the riverfront Gosnold's Hope Park.
Downtown Waterfront Condo W Boat Slip & Deck
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tennis court
- Terrace
Downtown Waterfront Condo W Boat Slip & Deck Elizabeth City villa is located merely a 5-minute walk from Charles Creek Park and offers guests to enjoy fisheries and darts. Located a mere 1.7 km from Cann Memorial Presbyterian Church, the 3-bedroom holiday home provides Wi-Fi and parking.
Downtown Waterfront Condo W Boat Slip & Deck
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Tennis court
- Terrace
Downtown Waterfront Condo W Boat Slip & Deck
Downtown Waterfront Condo W Boat Slip & Deck Elizabeth City villa is located merely a 5-minute walk from Charles Creek Park and offers guests to enjoy fisheries and darts. Located a mere 1.7 km from Cann Memorial Presbyterian Church, the 3-bedroom holiday home provides Wi-Fi and parking.
3Br Home 3 Mins To Airport And 11 Mins To Beach
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
The 3-bedroom 3Br Home 3 Mins To Airport And 11 Mins To Beach Norfolk is located nearly 25 minutes' walk from Norfolk Botanical Garden, giving access to various tourist spots nearby. With a maximum capacity of 6 guests, the property offers private parking.
3Br Home 3 Mins To Airport And 11 Mins To Beach
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Garden area
3Br Home 3 Mins To Airport And 11 Mins To Beach
The 3-bedroom 3Br Home 3 Mins To Airport And 11 Mins To Beach Norfolk is located nearly 25 minutes' walk from Norfolk Botanical Garden, giving access to various tourist spots nearby. With a maximum capacity of 6 guests, the property offers private parking.
The Sanctuary - Summer Breeze A114
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
- Outdoor swimming pool
Located 9 minutes' walk from Little Island Park, The Sanctuary - Summer Breeze A114 Virginia Beach villa features an outdoor swimming pool and can accommodate up to 6 guests. Located in proximity to Back Bay National Wildlife Refuge, the 2-bedroom holiday home provides high-speed Internet access and parking.
For active guests, there is a fitness classes, as well as a fitness room.
The Sanctuary - Summer Breeze A114
- BBQ facilities
- Air conditioning
- Flat-screen TV
- Tea and coffee facilities
- Fitness centre
- Outdoor swimming pool
The Sanctuary - Summer Breeze A114
Located 9 minutes' walk from Little Island Park, The Sanctuary - Summer Breeze A114 Virginia Beach villa features an outdoor swimming pool and can accommodate up to 6 guests. Located in proximity to Back Bay National Wildlife Refuge, the 2-bedroom holiday home provides high-speed Internet access and parking.
For active guests, there is a fitness classes, as well as a fitness room.
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Beach access
Classic Chesapeake Beachside Cottage W/ Porch!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Sun loungers
During the stay at Classic Chesapeake Beachside Cottage W/ Porch! Norfolk, guests can indulge in snorkelling and hiking or visit Ocean View Beach Park, located 3 km away. Offering guided snorkelling trips, the 2-bedroom holiday home can accommodate up to 4 people.
Classic Chesapeake Beachside Cottage W/ Porch!
- Cookware/ Kitchen utensils
- Free parking
- Express check-in/ -out
- Flat-screen TV
- Spa & wellness centre
- Sun loungers
Classic Chesapeake Beachside Cottage W/ Porch!
During the stay at Classic Chesapeake Beachside Cottage W/ Porch! Norfolk, guests can indulge in snorkelling and hiking or visit Ocean View Beach Park, located 3 km away. Offering guided snorkelling trips, the 2-bedroom holiday home can accommodate up to 4 people.
Great Wolf Lodge Williamsburg
- Restaurant
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Car park
US$ 19 per day
- Housekeeping
- Air conditioning
- Entertainment
- Heated swimming pool
Located nearly 5 minutes' walk from Great Wolf Lodge Williamsburg, Great Wolf Lodge Williamsburg features a heated pool with a hot tub. Offering a lift and a vending machine, this Williamsburg lodge is nestled 4.5 km from the 2705-acre Waller Mill Park.
Offering a treatment room, a hot tub, and an indoor pool as well as an aqua park, a bowling alley, and playground, Great Wolf Lodge Williamsburg has something for everyone. The spa treatments include aromatherapy, pedicure, and manicure after a busy day. There is ziplining, yoga classes, and bowling alley available on-site. This Williamsburg accommodation offers crafts, kids' outdoor play equipment, and interactive games for guests' entertainment.
Great Wolf Lodge Williamsburg
- Restaurant
-
Car park
US$ 19 per day
- Housekeeping
- Air conditioning
- Entertainment
- Heated swimming pool
Great Wolf Lodge Williamsburg
Located nearly 5 minutes' walk from Great Wolf Lodge Williamsburg, Great Wolf Lodge Williamsburg features a heated pool with a hot tub. Offering a lift and a vending machine, this Williamsburg lodge is nestled 4.5 km from the 2705-acre Waller Mill Park.
Offering a treatment room, a hot tub, and an indoor pool as well as an aqua park, a bowling alley, and playground, Great Wolf Lodge Williamsburg has something for everyone. The spa treatments include aromatherapy, pedicure, and manicure after a busy day. There is ziplining, yoga classes, and bowling alley available on-site. This Williamsburg accommodation offers crafts, kids' outdoor play equipment, and interactive games for guests' entertainment.
Are you in a hurry?
Here is a quick list of Vacation Rentals in Chesapeake, selected based on their rating
| Name of hotel | Accommodation Rating | Price, $ | |
| Econo Lodge Chesapeake Route 13 And I-464 |
5.0 / 10 (93 Reviews) |
From 52$ | |
| Spacious Chesapeake Home W/ Pool Table! |
9.5 / 10 (2 Reviews) |
From 302$ | |
| Dances Bay |
8.4 / 10 (199 Reviews) |
From 48$ | |
| Beach Luxury Oceanfront |
9.5 / 10 (68 Reviews) |
From 200$ | |
| Downtown Norfolk Loft |
9.8 / 10 (28 Reviews) |
From 315$ |
Frequently Asked Questions
Which Chesapeake vacation rentals are best for families?
Consider the Spacious Chesapeake Home W/ Pool Table! and Bright Chesapeake Home Near Shopping & Dining. These homes offer multiple bedrooms, a kitchen, and family-friendly spaces.
Book properties with backyards for kids' playtime and enjoy meals outside during sunny weather.
What vacation rentals near beaches are recommended in Chesapeake?
The Classic Chesapeake Beachside Cottage W/ Porch! and Beach Luxury Oceanfront are excellent choices near the beach. They provide easy access to coastal activities and beautiful views.
Visit the beach early in the morning to enjoy quieter shores and collect seashells before the crowds arrive.
Which vacation rentals are closest to downtown Chesapeake?
Check out Downtown Waterfront Condo W Boat Slip & Deck and Downtown Norfolk Loft. They place you right in the heart of the action, near dining and shopping.
Explore local shops and eateries within walking distance to fully experience downtown's vibrant atmosphere.
Are there Chesapeake vacation rentals with pools?
The Spacious Chesapeake Home W/ Pool Table! offers indoor recreation with a fun pool table and is great for families or groups. Look for vacation homes with outdoor pools for summer cooling.
Book during off-peak times in late spring for better rates and less crowded pools.
What vacation homes are suitable for larger groups?
Luxury Home 5 Bedroom 3 Ba Near Beaches And Venues is ideal for large families or groups. It has ample space and a fully equipped kitchen for group meals.
Consider cooking a meal together to bond while enjoying local ingredients from nearby markets.
Are there budget Chesapeake vacation rentals?
Look into Econo Lodge Chesapeake Route 13 And I-464 and Dances Bay for budget options. They offer basic amenities and are affordable for those looking to save.
Research dining options in local neighborhoods to find budget-friendly restaurants and avoid tourist traps.
Which vacation rentals in Chesapeake are pet-friendly?
Fenced Yard & Patio! 2,400-Sq-Ft Chesapeake Home is a great option that allows pets. Always check the specific pet policies for any added fees.
Make a list of pet-friendly parks nearby to enjoy outdoor activities with your furry friend.
What unique events take place in Chesapeake throughout the year?
The Chesapeake Jubilee is a popular annual event in May featuring food, music, and family activities. Attending this festival can be a highlight of your visit.
Plan accommodations nearby to avoid travel hassle and enjoy evening festivities without late-night drives.
How can I explore local cuisine while in Chesapeake?
Visit local favorites like Fish & Slips or The Egg Bistro. They offer unique dishes utilizing local ingredients.
Check out lunch specials during weekdays for cheaper dining options and a chance to try new menu items.
What is the best way to get around Chesapeake?
Renting a car is often the most convenient option due to limited public transit. This gives you the freedom to explore attractions at your own pace.
Consider booking a rental car that includes GPS; it can save you time navigating unfamiliar areas.