Jamestown Vacations from $821

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Your Jamestown Vacation

When you choose a Jamestown vacation package, you can kick back and enjoy your adventure to the fullest. Delve into the best parts of this fascinating city knowing that all the travel planning has been taken care of before you go. Hoping to do a little sightseeing? Spend some time enjoying well-known attractions like Lake Cumberland State Resort Park during your trip to Jamestown. A few clicks is all it takes to create the ideal Jamestown vacation on Expedia.

The Latest Jamestown vacation packages

Price found within the past 48 hours. Click for updated prices.
The Maple Retreat at Park Mammoth
Louisville Marriott Downtown
The Trail Hotel
Hancock House
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Jamestown Hotel Deals

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.

Jamestown KY
$498 nightly
The price is $549 total per night from Mar 17 to Mar 18
$549 total
Mar 17 - Mar 18
Total with taxes and fees
10/10 Exceptional! (162 reviews)
Great view with a beautiful Bald Eagle fly by! House had everything! Spent hours on the deck and could have used a bit of shade while waiting on the beautiful sunsets but we had a great time!

Reviewed on Mar 4, 2026

LAKE CUMBERLAND: AMAZING lake views year-round. Minutes to JAMESTOWN Marina, KY.
Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!

Jamestown KY
$508 nightly
The price is $560 total per night from Apr 1 to Apr 2
$560 total
Apr 1 - Apr 2
Total with taxes and fees
9.8/10 Exceptional! (26 reviews)
We had a wonderful stay here! There are two single bed rooms, and one room with two full (queen possibly?) bunk beds. So 6 big beds all together and the couch pulls out as well. Check in and check out instructions were clear. There were corn hole boards and bags available. The hot tub was great, ...

Reviewed on Oct 30, 2025

Cozy Lake Cumberland Retreat with hot tub, just above Jamestown Marina!
Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.

Jamestown KY
$320 nightly
The price is $353 total per night from Mar 9 to Mar 10
$353 total
Mar 9 - Mar 10
Total with taxes and fees
10/10 Exceptional! (196 reviews)
Everything was great

Reviewed on Feb 17, 2026

Above J’town Marina, LCKY. boat parking. 3 full baths. pool table. pet friendly.
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.

Find the Best Jamestown Vacation Packages

Things to do in and around Jamestown

Jamestown, Kentucky, is perfect for outdoor and romantic getaways, offering a variety of activities such as hiking trails, campgrounds, and recreational areas. Visitors can explore historic tours, embark on scenic driving adventures, and participate in archaeology tours. Don't forget to check for admission tickets to make the most of your experience in this charming town surrounded by beautiful scenery.

Shopping

If you're up for a drive, Somerset Mall, located 24 miles away, offers a variety of shops with a mix of business and family vibes. You’ll find everything from clothing to unique gifts, making it a great stop for souvenirs during your visit to Jamestown.

Recreation

Unwind at Taylor County Park, just 25 miles from Jamestown, where nature and tranquility blend seamlessly. Enjoy a round of golf at The Links Resort Golf Course nearby, offering outdoor sports vibes. For a cultural experience, visit Annex Theater, 29 miles away, featuring engaging performances for the whole family.

Adventure

At SomerSplash, 26 miles from Jamestown, enjoy thrilling water slides and family-friendly attractions for a fun-filled day. At Lillydale Recreation Area, 29 miles away, immerse yourself in nature with camping and outdoor activities that create lasting memories with loved ones in a beautiful setting.

Nightlife

Jamestown's nightlife offers a cozy atmosphere with local bars and restaurants. Enjoy live music at the Jamestown Pavilion or unwind at the nearby R & R Bar & Grill, where friendly locals gather for drinks and conversation, creating a warm and inviting experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Jamestown

Jamestown, Kentucky, is an idyllic destination for outdoor enthusiasts and romantic getaways, featuring stunning marinas and national parks. Visitors can enjoy family-friendly activities and beach experiences while exploring the area's rich history, including the Jamestown Rediscovery Project and insights into historic Jamestown. With its scenic landscapes and local attractions, Jamestown offers a perfect blend of adventure and relaxation for travelers seeking a memorable vacation.

  • Lake Cumberland State Resort Park: Experience the great outdoors at Lake Cumberland State Resort Park, where you can enjoy breathtaking scenery, hiking trails, and various water activities. It's perfect for adventure seekers and nature lovers alike, offering opportunities for fishing, boating, and camping amidst natural beauty.
  • Wolf Creek National Fish Hatchery: At the Wolf Creek National Fish Hatchery, immerse yourself in eco-friendly practices while learning about fish conservation. This environmental center provides educational tours that highlight the importance of aquatic ecosystems and sustainable fish farming, making it an enriching experience for all ages.
  • Lindsey Wilson College: Located 15 miles from Jamestown, Lindsey Wilson College boasts a rich history and vibrant campus culture. Explore its beautiful grounds and enjoy the educational and cultural events that foster community engagement and artistic expression.

Best time to go to Jamestown

The best time to visit Jamestown is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are moderately low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.2°F (1.8°C)Light RainMostly CloudyModerately LowSlightly Low
February39.6°F (4.2°C)Light RainMostly CloudyAverageAverage
March47.7°F (8.7°C)Light RainMostly CloudyAverageAverage
April56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
May65.8°F (18.8°C)Light RainMostly SunnyModerately HighAverage
June73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
July76.5°F (24.7°C)Light RainMostly SunnyModerately HighSlightly High
August75.0°F (23.9°C)Light RainMostly SunnyAverageSlightly High
September69.3°F (20.7°C)Light RainMostly SunnyAverageAverage
October58.5°F (14.7°C)Light RainMostly SunnyAverageAverage
November47.1°F (8.4°C)Light RainMostly SunnyModerately LowSlightly Low
December41.0°F (5.0°C)Light RainMostly CloudyModerately LowSlightly Low

Tips to save on your trip to Jamestown

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Jamestown.
  • Consider traveling to Jamestown during the low season (November to January) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Jamestown Essential Information

Language
English
Currency
U.S dollars
Population
1,800
Max Temp Winter
45ºF
Max Temp Summer
85ºF
Top Sights
Lake Cumberland State Resort Park and Wolf Creek National Fish Hatchery

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Frequently asked questions

How much does a Jamestown vacation package cost?
You can pick up a vacation package to this popular destination from $821 on Expedia. But how much your vacation to Jamestown costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Jamestown?
If you're looking to score a cheap Jamestown vacation package, consider planning a trip in January, February and August. You'll typically find better prices on accommodations and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Jamestown?
Typically, a handful of days is enough to visit the main sights during your Jamestown vacation. However, if you'd like to have some time to unwind or take day trips, consider extending your trip.
How to find the best Jamestown package deals?
Use Expedia's filters to help you find some great Jamestown package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or browse for Jamestown package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Jamestown vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still have the freedom to create a tailored Jamestown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Jamestown?
Enjoy incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for a spur-of-the-moment Jamestown escape.
Does Expedia offer Book Now, Pay Later Jamestown vacation packages?
Your Jamestown trip should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.