Jolly Island Vacation Rentals

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Our top choices for Jolly Island vacation rentals

$202 nightly
The price is $217
Dec 14 - Dec 15
Total with taxes and fees
Hiking & Snowmobile Trails On-site: Alton Retreat!
10.0 out of 10, Exceptional, (17)
"All excellent "
United States
Marc
$412 nightly
The price is $447
Dec 16 - Dec 17
Total with taxes and fees
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
9.8 out of 10, Exceptional, (36)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
$273 nightly
The price is $297
Dec 14 - Dec 15
Total with taxes and fees
Gorgeous Waterfront Condo with Lake Access & Views
2.0 star property
$286 nightly
The price is $310
Dec 27 - Dec 28
Total with taxes and fees
Quaint house in tranquil Wolfeboro perfect for getaway

Vacation Home in Ashland

Cold Spring Plymouth Resort
3.5 star property
9.2 out of 10, Wonderful, (161)
"We enjoy staying here, very conveniently located and comfortable."
United States
Angela
$125 nightly
The price is $136
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cold Spring Plymouth Resort
10.0 out of 10, Exceptional, (4)
"We had a perfect stay. Super cute cabin, clean and very comfortable.We thoroughly enjoyed or time there. Very easy process and would absolutely recommend and book again."
United States
Jessica G.
$171 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
9.6 out of 10, Exceptional, (15)
"Enjoyed our stay. "
United States
Ilene T.
$160 nightly
The price is $168
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cute Cedar Lodge Studio with Balcony & Lake Views!

Condo in Weirs Beach

2BR Condo with Private Patio
10.0 out of 10, Exceptional, (1)
"The property managers were very easy to get a hold of and responded to our request quickly."
United States
Kimberly
$185 nightly
The price is $201
Dec 14 - Dec 15
Total with taxes and fees
2BR Condo with Private Patio
9.2 out of 10, Wonderful, (17)
"Perfect location for Weirs beach, the boardwalk and concert venue. "
United States
Kathleen A.
$281 nightly
The price is $305
Dec 14 - Dec 15
Total with taxes and fees
Warm and Cozy Condo: Perfect for Fall Foliage Getaways!
10.0 out of 10, Exceptional, (1)
"Suxhh a beautiful and well kept home. Relaxing there was our favorite part of the trip!"
United States
Justin G.
$398 nightly
The price is $432
Dec 15 - Dec 16
Total with taxes and fees
Mountainside chalet with a sauna and beautiful views near Lake Winnipesaukee NH!
8.4 out of 10, Very Good, (17)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
$237 nightly
The price is $257
Dec 14 - Dec 15
Total with taxes and fees
Inviting condo in quiet locale with partial lake views, balcony & grilling area
10.0 out of 10, Exceptional, (6)
"Beautiful condo spacious and clean beautiful views loved the pool and hot tub! "
United States
Melissa D.
$262 nightly
The price is $284
Dec 17 - Dec 18
Total with taxes and fees
Cozy condo with WiFi, fitness room in enjoyable Laconia
9.0 out of 10, Wonderful, (2)
"We had a great time. Loved the cabin super cute. Neighborhood & neighbors very nice. The lake & private beaches were great. We enjoyed the hot tub & fire pit. I brought a few games, but you had a nice selection as well. Kitchen was very nice with everything we needed for some nice big breakfasts to start our day. We did run into a bit of a problem with the water running out. During showers, but we worked through it. Over all it was a great place. Thank you. Kim, Steve,Brianna,Cam & Brody "
United States
kim M.
$353 nightly
The price is $383
Dec 14 - Dec 15
Total with taxes and fees
Cozy Cottage on a Lake, near Gunstock Mountain
9.4 out of 10, Exceptional, (9)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
$318 nightly
The price is $345
Dec 16 - Dec 17
Total with taxes and fees
Modern Waterfront Condo with Views and Lake Access
$172 nightly
The price is $187
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Lake View Nook - Lake Winnipesaukee
9.8 out of 10, Exceptional, (13)
"Great place! Owners were very responsive with any questions we had. Per friendly was a plus. We would definitely stay here again."
United States
Shawn M.
$313 nightly
The price is $340
Dec 15 - Dec 16
Total with taxes and fees
Taigh Loch - Lakes Region Retreat!
9.6 out of 10, Exceptional, (21)
"Great location for seeing concerts."
United States
Kevin Y.
$230 nightly
The price is $249
Dec 22 - Dec 23
Total with taxes and fees
Lake view condo, Private Beach, Private concert entrance, pool
10.0 out of 10, Exceptional, (1)
"Everything was wonderful!! "
United States
Scott O.
$337 nightly
The price is $366
Dec 17 - Dec 18
Total with taxes and fees
Large Well Equipped Pet Friendly Home with Hot Tub | Bank of NH Pavilion 19 mins | Iconic Fall Foliage central location | Air Conditioning | Walk to Squam Lake Beach | Main Level Bedroom and Bathroom
$605 nightly
The price is $633
Dec 15 - Dec 16
Total with taxes and fees
Private Dock, Boat Access & Sunrise Views
$463 nightly
The price is $504
Dec 14 - Dec 15
Total with taxes and fees
Siena/Venice waterfront private units (2) with 2 Docks!
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.
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Top Jolly Island Hotel Reviews

Find out more about Jolly Island

Everything you need to know about Jolly Island vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Jolly Island vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Jolly Island vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Jolly Island vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Jolly Island. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Jolly Island in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Jolly Island rentals

At Expedia, we put the best Jolly Island vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Jolly Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Jolly Island vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Jolly Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find vacation rentals in Jolly Island?

Yes, you can find vacation rentals close to the most popular sights in Jolly Island, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Jolly Island?

Cold Spring Plymouth Resort: This vacation home rental near Jolly Island is located in the mountains and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. You can relax into your vacation with an outdoor tennis court and a hot tub.

What can I see and do in Jolly Island?

Explore the area and family-friendly sights such as Funspot Family Fun Center, or get out into nature at a spot like Lake Winnipesaukee. In the larger area, you’ll find Bank of New Hampshire Pavilion at Meadowbrook and Ellacoya State Park.

What are vacation rentals like in Jolly Island?

Vacation rentals are privately owned properties you can reserve for several days or more in Jolly Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for family trips or small group gatherings.