Book Hotels in Gwynn, VA

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Top Gwynn hotels

Gwynn's Island Cottage - Private Beach on the Chesapeake Bay!

Gwynn's Island Cottage - Private Beach on the Chesapeake Bay!

Grimstead VA
This cottage features a garden, laundry facilities, and barbecue grills.
"We had another excellent stay at Gwynn's Island cottage. We had wonderful views of Hills bay and great weather to go along with it. The cottage was clean and well stocked as always. Thanks again Cheri for letting us stay at this gem in Mathews County, Virginia and for being a wonderful hostess."

Reviewed on Jun 11, 2026

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Opens in a new windowGwynn's Island Cottage - Private Beach on the Chesapeake Bay!
Gwynn's Island Gem | Private Beach & Bay Views

Gwynn's Island Gem | Private Beach & Bay Views

Hudgins VA
This vacation home features barbecue grills.
"Hidden Gem, SCHWEET, AMAZING & Very Nice …. Was the answer from each of us who stayed!!"

Reviewed on Jun 4, 2026

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Opens in a new windowGwynn's Island Gem | Private Beach & Bay Views
Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
$432 nightly
The price is $500 total per night from Jun 29 to Jun 30
$500 total
Jun 29 - Jun 30
Total with taxes and fees
This cottage features a gym and a hot tub. Laundry facilities are provided for your convenience.
"Gorgeous property and excellent host!"

Reviewed on May 18, 2026

Opens in a new windowSmith Beach cottage w/ private sunset
Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Kimary Cove - Waterfront Relaxation and NO CLEANING FEE

Cobbs Creek VA
This vacation home features a garden, laundry facilities, and barbecue grills.
"My boyfriend and I were in town for a wedding, and while everyone else stayed in a hotel 30 min away, we stayed here! It was the loveliest time! The best thing was getting the chance to make breakfast, and sit out by the water under the trees! I absolutely would recommend this space!"

Reviewed on May 31, 2026

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Opens in a new windowKimary Cove - Waterfront Relaxation and NO CLEANING FEE
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $117 total per night from Jul 12 to Jul 13
$117 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features an indoor pool and a gym. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking. A 24-hour ...
"Everything was great. Everyone was polite."

Reviewed on Jun 11, 2026

Opens in a new windowHampton Inn Gloucester
The Tides Inn

The Tides Inn

4 out of 5
480 King Carter Dr Irvington VA
Fully refundableReserve now, pay when you stay
$413 nightly
The price is $447 total per night from Jun 22 to Jun 23
$447 total
Jun 22 - Jun 23
Total with taxes and fees
This smoke-free hotel features a private beach, a full-service spa, and a marina. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. There's ...
"Fantastic stay"

Reviewed on May 19, 2026

Opens in a new windowThe Tides Inn
Quality Inn Kilmarnock

Quality Inn Kilmarnock

2.5 out of 5
599 N Main St Kilmarnock VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Jul 5 to Jul 6
$124 total
Jul 5 - Jul 6
Total with taxes and fees
This hotel features an outdoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"Very clean, helpful staff, outside needs some upgrades, location great"

Reviewed on May 31, 2026

Opens in a new windowQuality Inn Kilmarnock
Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

3.5 out of 5
6639 Forest Hill Ave Gloucester VA
Fully refundable
$97 nightly
The price is $108 total per night from Jul 12 to Jul 13
$108 total
Jul 12 - Jul 13
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests ...
"The staff were pleasant but we had trouble getting help with a piece of medical equipment when we were ready to leave. The location is quiet and the breakfast was good. Our only real complaint was that the floor in our room wasn't that clean. It seemed a bit sandy underfoot from the get go."

Reviewed on Jun 9, 2026

Opens in a new windowHoliday Inn Express Gloucester by IHG
Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA

2.5 out of 5
226 Methodist Church Rd White Stone VA
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $126 total per night from Jul 1 to Jul 2
$126 total
Jul 1 - Jul 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are ...
"Dusty walls; many, many marks and stains on floor, walls, and woodwork. Parking in front of rooms full of cigarette butts and small trash. Price was cheap but definitely not worth the bargain. Needs extensive deep cleaning and repainting."

Reviewed on Jun 6, 2026

Opens in a new windowWhispering Pines by Hotel O Whitestone VA
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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.

Gwynn Hotel & Travel Guide\n

Book early as there are only a few options within an easy drive of Gwynn.

One of just a small number of accommodation options within walking distance to the sights of central Gwynn, is the Gwynn's Island RV Resort and Campground.

The Kilmarnock Inn is around 16 miles (25 kilometers) outside downtown Gwynn. Another hotel is the Hampton Inn Gloucester, which is 15 miles (24 kilometers) away. More accommodation options in the area are the Kilmarnock Hotel & Suites and the Comfort Inn Gloucester.

If you have the time, why not broaden your horizons and enjoy the myriad attractions around Coastal Virginia during your stay in this area? Admire Coastal Virginia's beaches and coastal plains. In addition you could discover the area's history museums and open-air museums. In this section of United States of America visitors might enjoy hiking, horse riding and quad biking.

When you and your family are in Chesapeake Bay, you should visit the Westmoreland State Park and spend the night in Montross, which is situated 50 miles (83 kilometers) to the northwest of the middle of Gwynn. The Washington & Lee Motel and The Inn at Stratford Hall are among your choices.

If you are really into sports and like to watch matches you might like to spend a day at Hampton Coliseum, which can be found 30 miles (52 kilometers) to the south of Gwynn. Wise visitors that would like to find accommodation options in the area around the stadium should choose between the Embassy Suites Hampton Roads- Hotel, Spa & Convention Center or the Hampton Bay Plaza and Suites.

Newport News - Williamsburg International Airport is a practical arrival point for flights, and is found 30 miles (44 kilometers) outside Gwynn's downtown area. Travelocity-listed accommodation nearby include Hampton Inn & Suites Newport News and Hilton Garden Inn Newport News.

Frequently asked questions

What are the top kid-friendly hotels in Gwynn?
From fun amenities to bigger rooms, kid-friendly hotels come with features that can help transform a good family vacation into an awesome one. These Gwynn options make vacationing with little ones easy: Island cottage getaway with deck and shared pier on the water. will help make your next trip the best one yet. It comes with a range of conveniences aimed at families, such as a nearby beach and cycling. Also look up Welcome to the North Shore of Gwynns Island on Chesapeake Bay. Pets stay free.. It comes with a nearby beach, cycling and ample opportunities to hang out together.
Where can I find cheap hotels in Gwynn?
At Travelocity you'll find really nice hotels in Gwynn at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Gwynn rather than in Gwynn. We may find you even better rates, too.
How do I find the best Gwynn hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Gwynn then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Gwynn?
The cheapest hotel in Gwynn is $108. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Gwynn?
There are 370 hotels in Gwynn on Travelocity.
What are the best hotels in Gwynn?
Gwynn has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Gwynn for you!
When is the best time to visit Gwynn?
If you want the joy of a fun-filled trip in peak season, visit Gwynn during March, July and August. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Gwynn?
Based on historic data is usually the cheapest month to visit Gwynn. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Gwynn?
There are multiple hotels in Gwynn that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Gwynn. We have plenty of kid-friendly hotels in Gwynn to choose from on Travelocity!
Why book a hotel in Gwynn through Travelocity?
Because we have the top hotels in Gwynn! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Gwynn on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Gwynn hotel reviews by fellow wanderers

Dockside Inn

Dockside Inn

5 out of 5
Posted 16 hours ago
Travelocity Verified Review
"We loved our stay! The property is very pretty and the room was beautiful! The amenities in the room were great and the breakfast items in the fridge were perfect! We’d definitely stay again."
A verified traveler stayed at Dockside Inn
Dockside Inn

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