Gwynn Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Gwynn

Holiday Inn Express Gloucester, an IHG Hotel
Holiday Inn Express Gloucester, an IHG Hotel
3.5 out of 5
6639 Forest Hill Ave, Gloucester, VA
Fully refundable
The price is S$172 per night from 3 Dec to 4 Dec
S$172
includes taxes & fees
3 Dec - 4 Dec
7.2/10 Good! (542 reviews)
"It was a nice place to stay, quiet and clean."

Reviewed on 10 Nov,2024

Holiday Inn Express Gloucester, an IHG Hotel
Best Western Kilmarnock Hotel
Best Western Kilmarnock Hotel
2.5 out of 5
599 N Main St, Kilmarnock, VA
Fully refundableReserve now, pay when you stay
The price is S$196 per night from 2 Dec to 3 Dec
S$196
includes taxes & fees
2 Dec - 3 Dec
7.8/10 Good! (619 reviews)
"I never give reviews but the girl who chcked us in last night at 10:40 Pm was so sweet. Pleasant.and kind with my two small. Sleepy children. I was in a rush and dont remenber her name but she really left an impression on me and my children. I also loved having a pizza hut classic nearby. We do not ..."

Reviewed on 3 Nov,2024

Best Western Kilmarnock Hotel
Hampton Inn Gloucester
Hampton Inn Gloucester
2.5 out of 5
6638 Forest Hill Ave, Gloucester, VA
Fully refundableReserve now, pay when you stay
The price is S$189 per night from 8 Dec to 9 Dec
S$189
includes taxes & fees
8 Dec - 9 Dec
9/10 Wonderful! (653 reviews)
"Liked everything but the tv options are more limited than I would like."

Reviewed on 23 Nov,2024

Hampton Inn Gloucester
See all 319 properties in Gwynn
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.

Frequently asked questions

How much does a Gwynn holiday package cost?
Explore the best of Gwynn from as low as . We offer a wonderful selection of flights, rental cars and hotels to suit your travel style. Pick up even more discounts when you add a couple of activities or tours to your package.
How do I get a cheap travel package to Gwynn?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, hotels, activities and rental cars — we’ve got them all. Pick the combination that suits you and watch your savings pile up. Of course, a travel package is never a one-size-fits-all. That’s why we offer more than 550 air carriers and 1,000,000 properties worldwide, which lets you customize your Gwynn holiday.
Where should I stay in Gwynn?
Gwynn boasts a number of terrific places to discover, including Gwynns Island Musuem. Spend your evenings in a hotel close by and make sightseeing hassle-free.
What are the top hotels in Gwynn?
Secure a room at Endless Chesapeake Bay Views. Rooftop Deck. Pets Stay Free. It’s one of this neighbourhood’s most popular properties. Another great option in Gwynn is Island Cottage Getaway With Deck And Shared Pier On The Water.
How far in advance should I book my Gwynn holiday?
Reward yourself with the biggest variety and the cheapest prices by booking your trip to Gwynn nice and early. Air carriers usually release flight tickets around 12 months in advance, so reserve your spot as soon as you can. That said, Expedia is committed to giving you the best deals around, so it’s always a good time to book your dream holiday!
What does an Expedia Gwynn travel package include?
With Expedia, you can choose a combination of car rentals, hotels and flights to build your ideal Gwynn package. Once you’ve made your booking, you can add on fun stuff like sightseeing tours and activities. Remember — the more you bundle, the more discounts you’ll get!
What should I know before booking a Gwynn travel package?
You can save big by bundling your hotels, flights and rental cars. Once you’ve created your package, add on fun stuff like tours and activities. Your next awesome adventure is only a few clicks away.
Can I choose my airline with a Gwynn Expedia holiday package?
Yes, you sure can. Expedia has access to more than 550 airline partners worldwide, so go with the carrier that’s a good fit for your budget and travel needs.
If I'm not able to travel, can I cancel my Gwynn holiday package?
If your holiday plans in Gwynn have changed, it’s good to know that it’s possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking is older than that, your hotel, airline or car rental company may charge a fee. For more details, check our Customer Service Portal.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.