Winery Hotels in Chesapeake Bay
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Chesapeake Bay Winery Hotels

Wedmore Place
5810 Wessex Hundred, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$150 nightly
The price is $170 total per night
$170 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of Wedmore Place have access to a winery, a full-service spa, and a gym. A stay here includes free parking. The front desk has multilingual staff that can help with tours or tickets, and offer advice about sights and eateries nearby. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Other amenities at this spa hotel include free WiFi in public areas, conference space, and a seasonal outdoor pool.
Pool
Breakfast included

Summer at the Rivah in Irvington! Come see for yourself!
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer

Kingsmill Resort
1010 Kingsmill Rd, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$298 nightly
The price is $330 total per night
$330 total
Jul 28 - Jul 29
Total includes taxes and fees
Kingsmill Resort features a golf course, a marina, and a full-service spa. Free parking is included with your stay. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this beach hotel include an indoor pool, a lazy river, and a children's pool.
Pool
Hot Tub

Hilton Vacation Club Greensprings Williamsburg
3500 Ludwell Pkwy, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $143 total per night
$143 total
Aug 3 - Aug 4
Total includes taxes and fees
Hilton Vacation Club Greensprings Williamsburg features an indoor pool, an outdoor pool, and a children's pool. A stay here includes free parking. Multilingual staff at the 24-hour front desk can assist with luggage storage, concierge services, and securing valuables. Other amenities at this golf resort include a gym, a sauna, and free WiFi in public areas.
Pool
Hot Tub

Hilton Vacation Club The Historic Powhatan Williamsburg
3601 Ironbound Rd, Williamsburg, VA
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $124 total per night
$124 total
Aug 12 - Aug 13
Total includes taxes and fees
Hilton Vacation Club The Historic Powhatan Williamsburg features an indoor pool, an outdoor pool, and a children's pool. If you plan to drive, free parking is available. The front desk is staffed 24 hours a day to help with securing valuables and tours/tickets. Other amenities at this golf resort include a 24-hour gym, outdoor tennis courts, and free WiFi in public areas.
Pool
Parking included

The Tides Inn
480 King Carter Dr, Irvington, VA
Free Cancellation
Reserve now, pay when you stay
$495 nightly
The price is $537 total per night
$537 total
Aug 24 - Aug 25
Total includes taxes and fees
The Tides Inn features a private beach, a marina, and a full-service spa. Front-desk staff can answer questions 24/7, and assist with dry cleaning/laundry, luggage storage, and tours or tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and an outdoor tennis court.
On private beach
Pool

Best Western Kilmarnock Hotel
599 N Main St, Kilmarnock, VA
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $157 total per night
$157 total
Jul 27 - Jul 28
Total includes taxes and fees
Guests of Best Western Kilmarnock Hotel enjoy an outdoor pool, free WiFi in public areas, and a business center. There's free parking if you drive. The front desk is staffed 24/7 to help with concierge services, and answer any questions about the accommodations. This hotel also has laundry facilities.
Pool
Breakfast included

Whispering Pines Motel
226 Methodist Church Rd, White Stone, VA
Guests of Whispering Pines Motel have access to free WiFi in public areas. You can take advantage of free parking if you drive. Friendly staff can provide front-desk service during limited hours, and also offer advice about sightseeing.
Pet friendly
Parking included

Super 8 by Wyndham Havre De Grace Aberdeen Area
929 Pulaski Hwy, I-95 Exit 89, Havre De Grace, MD
Free Cancellation
Reserve now, pay when you stay
$53 nightly
The price is $59 total per night
$59 total
Jul 30 - Jul 31
Total includes taxes and fees
Super 8 by Wyndham Havre De Grace Aberdeen Area features free WiFi in public areas and a vending machine. Free parking is included with your stay. Front-desk staff are standing by 24/7 to assist with any requests.
Breakfast included
Parking included

Colonial Gardens
1109 Jamestown Rd, Williamsburg, VA
Colonial Gardens features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you drive, put free parking to good use. Additional amenities include a refrigerator in a common area, a terrace, and a communal living room.
Parking included
Free WiFi

Williamsburg Sampler B & B
922 Jamestown Road, Williamsburg, VA
Guests of Williamsburg Sampler B & B enjoy access to free WiFi in public areas, coffee in a common area, and a meeting room. If you drive, put free parking to good use. Additional amenities include a library and a garden.
Pet friendly
Parking included

Red Roof Inn Perryville
61 Heather Lane, I-95 Exit 93, Perryville, MD
Free Cancellation
Reserve now, pay when you stay
$73 nightly
The price is $82 total per night
$82 total
Aug 4 - Aug 5
Total includes taxes and fees
Guests of Red Roof Inn Perryville enjoy access to free WiFi in public areas, meeting rooms, and a 24-hour business center. If you plan to drive, free parking is available. The front desk is staffed 24/7 to help with locker space, and answer any questions about the accommodations. Additional amenities include coffee/tea in a common area, a meeting room, and a computer station.
Pet friendly
Parking included

A Williamsburg White House
718 Jamestown Road, Williamsburg, VA
$219 nightly
The price is $247 total per night
$247 total
Jul 28 - Jul 29
Total includes taxes and fees
A local mainstay since 1904, A Williamsburg White House offers free WiFi in public areas, a library, and express check-in. Free parking is available if you drive. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this adults-only bed & breakfast include express check-out, free newspapers, and a fireplace in the lobby.
Breakfast included
Parking included

Budget Inn By OYO Nassawadox Hwy 13
7120 Lankford Hwy, Nassawadox, VA
Free Cancellation
Reserve now, pay when you stay
$84 nightly
The price is $92 total per night
$92 total
Aug 3 - Aug 4
Total includes taxes and fees
Guests staying at Budget Inn By OYO Nassawadox Hwy 13 enjoy free WiFi in public areas, laundry facilities, and a vending machine. Front-desk staff are standing by 24/7 to assist with any requests.
Pet friendly
Free WiFi

Cedars of Williamsburg Bed & Breakfast
616 Jamestown Road, Williamsburg, VA
$170 nightly
The price is $192 total per night
$192 total
Jul 30 - Jul 31
Total includes taxes and fees
Cedars of Williamsburg Bed & Breakfast features free WiFi in public areas, coffee in a common area, and microwave in a common area. If you decide to drive, there's free parking. Front-desk staff can assist with luggage storage and concierge services. Additional amenities include a refrigerator in a common area, an arcade/game room, and a library.
Breakfast included
Parking included
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Chesapeake Bay hotels essential information
Accommodation | 14,960 hotels |
---|---|
Lowest Price | $59 |
Highest Price | $537 |
Popular hotels | Wedmore Place, Summer at the Rivah in Irvington! Come see for yourself!, Kingsmill Resort, Hilton Vacation Club Greensprings Williamsburg, Hilton Vacation Club The Historic Powhatan Williamsburg, The Tides Inn, Best Western Kilmarnock Hotel, Whispering Pines Motel, Super 8 by Wyndham Havre De Grace Aberdeen Area, Colonial Gardens, Williamsburg Sampler B & B, Red Roof Inn Perryville, A Williamsburg White House, Budget Inn By OYO Nassawadox Hwy 13, Cedars of Williamsburg Bed & Breakfast |
Recent Winery Hotels Reviews

Hotel Arboretum
5/5 Excellent
"I was there overnight, so It was a quick stay. I loved the cleanliness, the breakfast, the staff, and the beauty of the suite."
A verified traveler stayed at Hotel Arboretum
Posted 22 hours ago
Other Winery Hotels
Areas Of Chesapeake Bay
Hotels Near
Hotel Themes
Flights To
Top Trending
Hotels
- All Inclusive Resorts & Hotels in Pocono Mountains
- Romantic Getaways & Hotels in Pocono Mountains
- Hotels with Hot Tubs in Pocono Mountains
- Hotels in Florida Keys
- Kid Friendly Hotels in Gulf Coast
- Waterpark Hotels & Resorts in Gulf Coast
- Spa Resorts & Hotels in Pocono Mountains
- Hotels with a Lazy River in Southern California
- Casino Resorts & Hotels in Northern California
- All Inclusive Resorts & Hotels in Southeastern United States
- All Inclusive Resorts & Hotels in Western United States
- Hotels with Waterslides in Southern California
- Beach Resorts & Hotels in Florida Keys
- Spa Resorts & Hotels in Southern California
- Kid Friendly Hotels in Northern California
- Hotels in Pocono Mountains
- Waterpark Hotels & Resorts in Pocono Mountains
- Hotels with Waterslides in Florida Keys
- All Inclusive Resorts & Hotels in Northern California
- Beach Resorts & Hotels in Northern California
- Hotels with Hot Tubs in Southern California
- Beach Resorts & Hotels in Gulf Coast
- Spa Resorts & Hotels in Northern California
- Hotels with an Indoor Pool in Southern California
- Cheap Hotels in Florida Keys
- Hotels with an Indoor Pool in Pocono Mountains
- All Inclusive Resorts & Hotels in Florida Keys
- Hotels with Hot Tubs in Quad Cities
Flights
Packages