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Top Gwynn hotels

Waterfront Cottage w Private Beach on Chesapeake Bay!

Waterfront Cottage w Private Beach on Chesapeake Bay!

Grimstead VA
This cottage features a garden, laundry facilities, and barbecue grills.
"This was our fifth stay here and it somehow keeps getting better! The Cottage has everything you could ever want for a vacation, including amazing restaurants close by. The beautiful sunsets every night, the private beach with clear Hills Bay water, the peacefulness — and we get to enjoy it all with ..."

Reviewed on Aug 30, 2026

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Opens in a new windowWaterfront Cottage w Private Beach on 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.
"We enjoyed our stay. Home was clean with good A/C and the bay breeze also nice outside. My wife really loved the sunrise. The island is a nice quiet get away spot, but still within 10-40 min. or so of some nice small town's or a day trip to York / Williamsburg. Very nice sandy beach, just would have ..."

Reviewed on Jul 27, 2026

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Opens in a new windowGwynn's Island Gem | Private Beach & Bay Views
Cottage on a Private Island in the York River

Cottage on a Private Island in the York River

Gloucester Point VA
This cottage features a garden, laundry facilities, and barbecue grills.
"Our stay was wonderful! Husband had a great time fishing :) Owners are quick to respond, very helpful and extremely kind. Thank you so much!!"

Reviewed on Jul 25, 2026

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Opens in a new window Cottage on a Private Island in the York River
Warner Hall

Warner Hall

3 out of 5
4750 Warner Hall Road Gloucester VA
$198 nightly
The price is $221 total per night from Sep 30 to Oct 1
$221 total
Sep 30 - Oct 1
Total with taxes and fees
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free full breakfast each morning.
"Great experience at this lovely historic inn. Close to Yorktown and all the sights. Would definitely go back again. Comfortable beds and pillows, restful nights, great breakfasts. Love it!"

Reviewed on Aug 28, 2026

Opens in a new windowWarner Hall
Smith Beach cottage w/ private sunset

Smith Beach cottage w/ private sunset

Cape Charles VA
$381 nightly
The price is $445 total per night from Sep 2 to Sep 3
$445 total
Sep 2 - Sep 3
Total with taxes and fees
This cottage features a gym and a hot tub. Laundry facilities are provided for your convenience.
"The location & view were everything and we quite satisfied w that. On the flip side these were our observations-*Flower beds sadly overgrown and whole yard needs a good trim. *Brick path to hot tub needs attention, or just removed*Window unit in sunroom completely rusted & unusable. Should be removed ..."

Reviewed on Aug 25, 2026

Opens in a new windowSmith Beach cottage w/ private sunset
Hampton Inn Gloucester

Hampton Inn Gloucester

2.5 out of 5
6638 Forest Hill Ave Gloucester VA
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $110 total per night from Sep 20 to Sep 21
$110 total
Sep 20 - Sep 21
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 ...
"Very nice lady checked us in, all in all a positive experience"

Reviewed on Aug 28, 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
$335 nightly
The price is $362 total per night from Sep 27 to Sep 28
$362 total
Sep 27 - Sep 28
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 ...
"Wait staff seemed to be stretched but did the best they could."

Reviewed on Aug 30, 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 refundable
$104 nightly
The price is $118 total per night from Sep 20 to Sep 21
$118 total
Sep 20 - Sep 21
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 ...
"Good service, clean rooms,"

Reviewed on Aug 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
$91 nightly
The price is $101 total per night from Sep 3 to Sep 4
$101 total
Sep 3 - Sep 4
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 ...
"I stay here every time I am in town. (The room wasn’t cleaned properly. Debris on floor in bathroom and entry door way. Shower curtain was dirty on bottom and black substance on top wear rod is inserted.) those were the only issues. Still one of my favorite stays in Gloucester"

Reviewed on Aug 31, 2026

Opens in a new windowHoliday Inn Express Gloucester by IHG
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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 $101. 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 371 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

Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG

4 out of 5
Posted 2 hours ago
Travelocity Verified Review
"I stay here every time I am in town. (The room wasn’t cleaned properly. Debris on floor in bathroom and entry door way. Shower curtain was dirty on bottom and black substance on top wear rod is inserted.) those were the only issues. Still one of my favorite stays in Gloucester"
A verified traveler stayed at Holiday Inn Express Gloucester by IHG
Holiday Inn Express Gloucester by IHG

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