Winnisquam Holiday Rentals

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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Winnisquam holiday rentals

Outdoor dining
Modern Waterfront Condo with Views and Lake Access

Condo in Tilton

Modern Waterfront Condo with Views and Lake Access
9.4 out of 10, Exceptional, (10)
"Beautiful place, would be amazing to stay during the summer! "
United States
Liriana
The price is HK$1,008
HK$2,671 total
includes taxes & fees
4 Jan - 5 Jan 2026
Modern Waterfront Condo with Views and Lake Access
Private kitchen
9 Lake Street

Apartment in Wolfeboro

9 Lake Street
3.0 star property
10.0 out of 10, Exceptional, (1)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is HK$1,096
HK$1,906 total
includes taxes & fees
16 Jan - 17 Jan 2026
9 Lake Street
Exterior
Cold Spring Plymouth Resort

Holiday Home in Ashland

Cold Spring Plymouth Resort
3.5 star property
9.2 out of 10, Wonderful, (167)
"The apartment was great, we enjoyed the pool, jacuzzi and sauna, and the staff were super nice!!"
United States
Jenn
The price is HK$1,019
HK$1,106 total
includes taxes & fees
13 Jan - 14 Jan 2026
Cold Spring Plymouth Resort
Property grounds
Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Cottage in Wolfeboro

Grandmas Cottage on the River and the Rail Trail in Wolfeboro
10.0 out of 10, Exceptional, (17)
"All excellent "
United States
Marc
The price is HK$1,371
HK$3,538 total
includes taxes & fees
7 Jan - 8 Jan 2026
Grandmas Cottage on the River and the Rail Trail in Wolfeboro
Property grounds
Gorgeous Waterfront Condo with Lake Access & Views

Condo in Tilton

Gorgeous Waterfront Condo with Lake Access & Views
9.8 out of 10, Exceptional, (36)
"Great area, lake side is beautiful, responsive host. "
United States
jamie
The price is HK$797
HK$2,307 total
includes taxes & fees
5 Jan - 6 Jan 2026
Gorgeous Waterfront Condo with Lake Access & Views
Fridge, microwave, oven, stovetop
Cute Cedar Lodge Studio with Balcony & Lake Views!

Apartment in Weirs Beach

Cute Cedar Lodge Studio with Balcony & Lake Views!
9.6 out of 10, Exceptional, (15)
"Enjoyed our stay. "
United States
Ilene T.
The price is HK$482
HK$1,277 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cute Cedar Lodge Studio with Balcony & Lake Views!
Terrace/patio
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath

Cottage in Wolfeboro

Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
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.
The price is HK$1,294
HK$1,598 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cottage 10 - 1 Bedroom w/ Loft / 1 Bath
Fridge, microwave, oven, stovetop
Cozy Winter Escape

Condo in Weirs Beach

Cozy Winter Escape
9.2 out of 10, Wonderful, (17)
"Perfect location for Weirs beach, the boardwalk and concert venue. "
United States
Kathleen A.
The price is HK$770
HK$2,362 total
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Winter Escape
Balcony
Inviting condo in quiet locale with partial lake views, balcony & grilling area

Condo in Gilford

Inviting condo in quiet locale with partial lake views, balcony & grilling area
8.4 out of 10, Very good, (17)
"Everything was just as listed, full amenities and cleanliness."
United States
John C.
The price is HK$591
HK$2,069 total
includes taxes & fees
5 Jan - 6 Jan 2026
Inviting condo in quiet locale with partial lake views, balcony & grilling area
Private kitchen
Cozy Cottage on a Lake, near Gunstock Mountain

Cottage in Gilmanton

Cozy Cottage on a Lake, near Gunstock Mountain
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.
The price is HK$1,329
HK$3,079 total
includes taxes & fees
6 Jan - 7 Jan 2026
Cozy Cottage on a Lake, near Gunstock Mountain
Beach
NEW Lakefront Escape Private Dock & Lake Views

Apartment in Alton

NEW Lakefront Escape Private Dock & Lake Views
9.8 out of 10, Exceptional, (10)
"We stayed here because we were in town for a concert in Gilford and it was great! Perfect location, close to the venue and the lake was beautiful. It was lovely waking up to seeing the sparkling water. Would stay again. "
United States
Anna S.
The price is HK$926
HK$2,331 total
includes taxes & fees
20 Jan - 21 Jan 2026
NEW Lakefront Escape Private Dock & Lake Views
Marina
Retro Pines Getaway - Lake Winnipesaukee

Condo in Weirs Beach

Retro Pines Getaway - Lake Winnipesaukee
The price is HK$654
HK$1,537 total
includes taxes & fees
27 Jan - 28 Jan 2026
Retro Pines Getaway - Lake Winnipesaukee
Beach nearby
Lake Access, Poolside Deck & Ski Nearby

Condo in Gilford

Lake Access, Poolside Deck & Ski Nearby
8.0 out of 10, Very good, (12)
"Clean, comfortable and perfect location for our needs. Host is very responsive and easy to work with."
United States
Dan K.
The price is HK$731
HK$1,561 total
includes taxes & fees
15 Jan - 16 Jan 2026
Lake Access, Poolside Deck & Ski Nearby
Sun-loungers, beach towels
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort

Condo in Gilford

Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
9.6 out of 10, Exceptional, (21)
"Great location for seeing concerts."
United States
Kevin Y.
The price is HK$805
HK$1,944 total
includes taxes & fees
7 Jan - 8 Jan 2026
Lake view, Private Beach, Private concert entrance, pool, Gunstock ski resort
Property grounds
2 Bdrm Cozy Cottage #1 -Water Access and Dock on Lake Winnipesaukee - Meredith

Cabin in Meredith

2 Bdrm Cozy Cottage #1 -Water Access and Dock on Lake Winnipesaukee - Meredith
2.0 star property
The price is HK$1,392
HK$3,155 total
includes taxes & fees
5 Jan - 6 Jan 2026
2 Bdrm Cozy Cottage #1 -Water Access and Dock on Lake Winnipesaukee - Meredith
Terrace/patio
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

Holiday Home in Holderness

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
10.0 out of 10, Exceptional, (1)
"Everything was wonderful!! "
United States
Scott O.
The price is HK$1,609
HK$2,843 total
includes taxes & fees
5 Jan - 6 Jan 2026
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
Fridge, microwave, oven, stovetop
19 Mile Bay - Tuftonboro - Lake Winnipesaukee

Holiday Home in Tuftonboro

19 Mile Bay - Tuftonboro - Lake Winnipesaukee
10.0 out of 10, Exceptional, (18)
"My stay there with my family was amazing with near by beaches and great views of the lakes. The house was very clean when we arrived and the back yard with cornhole boards was a plus over all this house and location was awesome!!"
United States
Oudom S.
The price is HK$1,829
HK$4,583 total
includes taxes & fees
5 Jan - 6 Jan 2026
19 Mile Bay - Tuftonboro - Lake Winnipesaukee
Exterior
Hot Tub, Arcade, Near Lake & Slopes

Holiday Home in Gilford

Hot Tub, Arcade, Near Lake & Slopes
The price is HK$1,479
HK$5,206 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hot Tub, Arcade, Near Lake & Slopes
Marina
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake

Holiday Home in Alton

Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
9.6 out of 10, Exceptional, (4)
"My brothers and I had an incredible time on the lake and experienced the local amenities. The individual apartments were perfect for our needs and allowed for everyone to have their own space. The property was well managed and maintained. I would highly recommend this location for anyone looking to enjoy lake Winni! Thank you, Ron"
United States
Ronnie G.
The price is HK$3,265
HK$8,714 total
includes taxes & fees
12 Jan - 13 Jan 2026
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
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 Winnisquam Hotel Reviews

The Wolfeboro Inn

The Wolfeboro Inn

10/10 Excellent
"Very clean room, pleasant staff, great location."
sheila 1-night trip
Posted 4 days ago
The Wolfeboro Inn

Find out more about Winnisquam

Search for holiday rentals in Winnisquam on Expedia! You can easily find your home rentals, villas, holiday apartments in Winnisquam using one of the methods below:

  • View our selection of featured holiday rentals in Winnisquam
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  • Enter your travel dates to view the best deals on holiday rentals in Winnisquam while they last

Look no further and take a look at our great range of rental properties in Winnisquam!

Frequently asked questions

Are there holiday rentals in Winnisquam?

Yes, there are holiday rentals close to the most popular sights in Winnisquam, or you can select a more secluded option if you're looking for a relaxing stay. Winnisquam is known for its shopping.

What are some of the best holiday rentals that Winnisquam has to offer?

Cold Spring Plymouth Resort: This holiday home rental outside of Winnisquam is located in the mountains, and has an outdoor pool, a fireplace and a BBQ 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 holiday with an outdoor tennis court and 1 hot tub.

How many holiday rentals are there in Winnisquam?

Choose from 24 Expedia holiday rentals in Winnisquam for a memorable holiday.

What’s there to see and do in Winnisquam?

While exploring the area, visit family-friendly sights like Funspot Family Fun Center, or get outside and enjoy nature at Lake Winnisquam. In the wider area, you’ll find Opechee Park Cove Beach and Opechee Point Beach and Tanger Outlets Tilton.

What’s a holiday rental in Winnisquam like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winnisquam. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.