Ossipee holiday homes

We found 2,598 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Ossipee that are perfect for your trip. Holiday rentals offer the amenities that you expect for your stay with friends, family or just your pet, such as cable TV and a washer and dryer. What you'll find is a property to rent for everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Ossipee

Showing deals for:18 Dec - 25 Dec

3 season porch on main level, store all your gear here
Eat in kitchen
The lower level which walks out to firepit area
Living room
Exceptional
(53 reviews)

1.5 miles to Gunstock. Great for larger groups or multiple families

Gilford

8% off
NZ$6,115
for 7 nights, 1 chalet
NZ$874 per night
includes taxes & fees
1.5 miles to Gunstock. Great for larger groups or multiple families
Living area
Exterior
Dining
Private kitchen
Exceptional
(25 reviews)

Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room

Laconia

8% off
NZ$23,196
for 7 nights, 1 home
NZ$3,314 per night
includes taxes & fees
Lake Winnipesaukee, Boat Dock, Summer Hot Tub and Game Room
Private kitchen
Dining
Outdoor dining
Living area
Exceptional
(10 reviews)

Spacious Lakes Region Retreat—Game Room & Gazebo

Meredith

8% off
NZ$13,520
for 7 nights, 1 home
NZ$1,931 per night
includes taxes & fees
Spacious Lakes Region Retreat—Game Room & Gazebo
Indian Mound Golf Club
Sap House Meadery in Ossipee
Living room
Living room
Exceptional
(44 reviews)

Beautiful property with Mountain View & privacy. Near slopes, trails & eateries!

West Ossipee

8% off
NZ$4,579
for 7 nights, 1 home
NZ$654 per night
includes taxes & fees
Beautiful property with Mountain View & privacy. Near slopes, trails & eateries!
Sunrise from the deck
Beautiful lake views and private dock
No wake cove perfect for swimming, floating and wading
Evening from the deck
Exceptional
(7 reviews)

Lakefront home with private dock on Lake Ossipee in Freedom, NH sleeps up to 10

Freedom

8% off
NZ$6,076
for 7 nights, 1 home
NZ$868 per night
includes taxes & fees
Lakefront home with private dock on Lake Ossipee in Freedom, NH sleeps up to 10
Living area
sitting on deck overlooking diamond, rattlesnake island and Wolfboro neck
view from kitchen
Private kitchen
Exceptional
(170 reviews)

Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile

GILFORD

8% off
NZ$5,810
for 7 nights, 1 home
NZ$830 per night
includes taxes & fees
Ski Gunstock 3 minutes away then relax overlooking lakeWinnipesaukee mile
Hot Tub view of courtyard
3 season front porch
Exterior
Living area
Exceptional
(26 reviews)

Troy's Cabin in North Conway with Hot Tub

Conway

9% off
NZ$4,711
for 7 nights, 1 cabin
NZ$673 per night
includes taxes & fees
Troy's Cabin in North Conway with Hot Tub
Fireplace seating area - dining area and kitchen in background
Property from the lake
Property from end of dock
Family room
Exceptional
(155 reviews)

Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more

Alton Bay

8% off
NZ$9,776
for 7 nights, 1 home
NZ$1,397 per night
includes taxes & fees
Lake Winnipesaukee Waterfront! Family Friendly, Amazing View, HotTub,Kayaks+more
Exterior
Comfy seats around one of two fire pits.
View of the house from the beach.
12c coffee pot, keurig, 4 slice toaster, blender, etc.
Exceptional
(188 reviews)

Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey

Moultonboro

8% off
NZ$5,147
for 7 nights, 1 home
NZ$735 per night
includes taxes & fees
Great multi-generational! Family/Pet-2 Kings,Lg Loft, Pool Tbl/P pong/Air Hockey
Dining
Dining
Interior
Private kitchen
Exceptional
(18 reviews)

The Nordic - 3 Bed Mountain Home in Bartlett, NH

Bartlett

8% off
NZ$8,388
for 7 nights, 1 cabin
NZ$1,198 per night
includes taxes & fees
The Nordic - 3 Bed Mountain Home in Bartlett, NH
Dining area with view of lake.
View of deck and lake from living room window.
Exterior
Dock for you boat
Exceptional
(39 reviews)

Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5

Denmark

12% off
NZ$3,591
for 7 nights, 1 cottage
NZ$513 per night
includes taxes & fees
Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5
Room
Living area
Exterior
Dining
Exceptional
(10 reviews)

Quiet Lake Retreat with Fireplace and short walk to the beach

Moultonborough

8% off
NZ$4,438
for 7 nights, 1 cottage
NZ$634 per night
includes taxes & fees
Quiet Lake Retreat with Fireplace and short walk to the beach
Kitchen
Living room
Kitchen/Dinning area
Living room
Exceptional
(75 reviews)

Perfect location - very close to Skiing, Hiking, Beach, Storyland - 4BR,3 BA

Bartlett

8% off
NZ$5,546
for 7 nights, 1 home
NZ$792 per night
includes taxes & fees
Perfect location - very close to Skiing, Hiking, Beach, Storyland - 4BR,3 BA
Interior
Property grounds
Dining
Living area
Exceptional
(28 reviews)

Direct Lakefront. Swim/Fish/Kayak/Hike/Relax White Mountains & NH Lakes Region.

Effingham

8% off
NZ$2,912
for 7 nights, 1 cottage
NZ$416 per night
includes taxes & fees
Direct Lakefront. Swim/Fish/Kayak/Hike/Relax White Mountains & NH Lakes Region.
Room
Terrace/patio
Living area
Living area
Exceptional
(51 reviews)

Kezar Lake 4-Bedroom 4-Season House w/Easy Access to Pleasant Mtn/Sunday River

Lovell

8% off
NZ$3,949
for 7 nights, 1 home
NZ$564 per night
includes taxes & fees
Kezar Lake 4-Bedroom 4-Season House w/Easy Access to Pleasant Mtn/Sunday River
Dining room
Terrace/patio
Pool
Living area
Exceptional
(25 reviews)

Bear Brook Lodge - Large house with pool

Bartlett

13% off
NZ$14,905
for 7 nights, 1 home
NZ$2,129 per night
includes taxes & fees
Bear Brook Lodge - Large house with pool
Room
Exterior
the driveway
beautiful views from the upstairs bedroom
Exceptional
(49 reviews)

Spacious New Hampshire mountain waterfront get away house. Boats & private docks

Alton

8% off
NZ$10,946
for 7 nights, 1 home
NZ$1,564 per night
includes taxes & fees
Spacious New Hampshire mountain waterfront get away house. Boats & private docks
Private kitchen
Private kitchen
Living area
Property grounds
Exceptional
(16 reviews)

NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE

Wolfeboro

8% off
NZ$8,234
for 7 nights, 1 home
NZ$1,176 per night
includes taxes & fees
NEWLY REMODELED N Main St. Close to TOWN and LAKE WINNIPESAUKEE
Interior
Private kitchen
Exterior
Living area
Exceptional
(41 reviews)

Madison Cottage, 2 Bedroom,

Madison

17% off
NZ$1,897
for 7 nights, 1 cottage
NZ$271 per night
includes taxes & fees
Madison Cottage, 2 Bedroom,
Snowmobilers on Shannon Brook heading towards Lake Winnipsaukee.
Property grounds
Private kitchen
Cable TV!!
Wonderful
(36 reviews)

Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6

Moultonborough

8% off
NZ$3,563
for 7 nights, 1 home
NZ$509 per night
includes taxes & fees
Direct Water Access to Lake! w/ Boat Dock, Heat, AC, TV & Internet, Sleeps 6
fire pit and grilling area.
Interior
Private kitchen
Second kitchen and living area in the addition completed in 2020
Exceptional
(15 reviews)

Perfect Location in North Conway Village

Conway

8% off
NZ$7,510
for 7 nights, 1 home
NZ$1,073 per night
includes taxes & fees
Perfect Location in North Conway Village
Dining
Living area
Interior
Property grounds
Exceptional
(10 reviews)

Cozy 4 bd/3.5 br in N. Conway by town & mountains

Conway

5% off
NZ$5,899
for 7 nights, 1 home
NZ$843 per night
includes taxes & fees
Cozy 4 bd/3.5 br in N. Conway by town & mountains
Interior
Private kitchen
Property grounds
Exterior detail
Exceptional
(11 reviews)

Charming 3-bedroom house in lovely Moultonborough with WiFi, AC

Moultonborough

8% off
NZ$3,561
for 7 nights, 1 home
NZ$509 per night
includes taxes & fees
Charming 3-bedroom house in lovely Moultonborough with WiFi, AC
Entrance to unit to left
Dining area and stairs up to loft and master bedroom
Master Bedroom
Fireplace in living room
Exceptional
(47 reviews)

Mt. Washington Valley Get Away - near Attitash Ski Resort & North Conway

Hart's Location

8% off
NZ$3,561
for 7 nights, 1 home
NZ$509 per night
includes taxes & fees
Mt. Washington Valley Get Away - near Attitash Ski Resort & North Conway

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Ossipee getaway

Learn about the unique charm of Ossipee with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Ossipee

Do you want to discover things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Ossipee a fun place to get away to. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Stand Up Paddleboard NH (10.4 mi / 16.7 km)
  • King Pine Ski Area (13 mi / 20.9 km)
  • Ellacoya State Park (14.3 mi / 22.9 km)
  • Gunstock Mountain Resort (16 mi / 25.7 km)
  • Sandwich Creamery (18.9 mi / 30.4 km)
  • Province Lake Golf Course (7 mi / 11.2 km)

Exploring the natural landscape of Ossipee

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Ossipee. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Belleau Lake (6.2 mi / 10 km)
  • Ossipee Lake Trail (6.3 mi / 10.1 km)
  • Lake Wentworth (6.4 mi / 10.2 km)
  • Allen Albee Beach (6.6 mi / 10.6 km)
  • Ossipee Lake (7.3 mi / 11.7 km)
  • Balch Pond (9.2 mi / 14.7 km)

Travelling to and around Ossipee

The nearest airport is in Laconia, NH (LCI-Laconia Municipal), located 17.3 mi (27.8 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Fryeburg, ME (FRY-Eastern Slopes Regional), which is 22.6 mi (36.4 km) away.

Frequently asked questions

What is the best area to stay in Ossipee when booking a holiday rental?
When considering a holiday rental in Ossipee, New Hampshire, the area surrounding Ossipee Lake is often regarded as the best choice. This picturesque neighbourhood offers a delightful blend of natural beauty and recreational activities. Guests can enjoy the stunning views of the lake and the surrounding mountains, making it a superb spot for outdoor enthusiasts.One of the top attractions in this area is the Ossipee Lake Public Beach, where visitors can swim, sunbathe, and engage in various water sports. Additionally, the nearby White Mountain National Forest provides ample opportunities for hiking and exploring the great outdoors, showcasing New Hampshire's breathtaking landscapes.In terms of accommodation, there are numerous properties available, ranging from cosy cabins to larger family homes, suiting different group sizes and preferences.
Where are the best areas for renting a beach house in Ossipee?
For renting a beach house in Ossipee, the area around Ossipee Lake is an excellent choice. This picturesque region features a variety of holiday rentals, ranging from charming cottages to spacious lakefront homes. Many properties boast amenities such as private docks, outdoor patios, and fire pits, great for relaxing evenings by the water after a day of swimming or boating.The nearby Ossipee Lake State Park offers sandy beaches and picnic areas, making it a great spot for families. Rentals in this vicinity often provide easy access to the park's recreational facilities, including hiking trails and fishing spots. Additionally, properties may come equipped with fully stocked kitchens and laundry facilities, suiting the needs of families or groups looking for a comfortable stay.For those who enjoy a more rustic experience, the surrounding areas of Freedom and Effingham offer a selection of cabins and older homes with a traditional New England charm.
Where are the best Ossipee ski resort rentals?
For the best ski resort rentals near Ossipee, New Hampshire, travellers should consider the nearby Mount Cranmore area in North Conway, which is approximately a 30-minute drive away. This popular ski destination offers a variety of accommodations, including charming lodges and modern condos that cater to families and groups. Many of these properties feature amenities such as fireplaces, fully equipped kitchens, and ski storage, ensuring a comfortable stay after a day on the slopes.In the Ossipee region itself, visitors can find quaint cabins and homes located in peaceful surroundings. These rentals typically offer rustic charm, with amenities like outdoor fire pits, private decks for enjoying the scenic views, and easy access to local hiking trails. The proximity to the Ossipee Lake area adds an extra layer of appeal, as guests can enjoy winter activities such as ice fishing and snowshoeing.For those looking to explore beyond skiing, the charming town of Wolfeboro, located on the eastern shore of Lake Winnipesaukee, is also within driving distance. Here, accommodations range from lakeside cottages to historic inns, often equipped with modern conveniences like Wi-Fi and central heating.
What is the most popular type of holiday rental accomodation in Ossipee?
In Ossipee, holiday houses are the most popular type of holiday rental, with around 14 available in the area. These houses are typically situated near the beautiful Ossipee Lake and the surrounding natural landscapes, providing a serene escape for travellers. Most holiday houses come with amenities such as fully equipped kitchens, spacious living areas, and outdoor decks or patios—ideal for enjoying the fresh air and scenic views.In addition to holiday houses, there are several cottages and apartments available, which offer a more intimate setting for smaller groups or couples. Cottages often feature charming interiors with rustic decor, while apartments provide convenient access to local attractions.
Are there any family house rentals in Ossipee?
In Ossipee, New Hampshire, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features properties that often include spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas where kids can play and explore. Many homes also come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.Visitors can enjoy the natural beauty of the surrounding landscape, with nearby attractions like the Ossipee Lake and the White Mountain National Forest, superb for outdoor activities such as hiking, swimming, and fishing.
Can I rent a holiday home with a pool or hot tub in Ossipee?
In Ossipee, New Hampshire, there are several holiday homes available for rent that feature pools and hot tubs. This picturesque area, known for its scenic landscapes and proximity to Lake Ossipee, offers a range of properties ideal for a relaxing getaway. Many of these rentals come equipped with private pools and hot tubs, superb for unwinding after a day of outdoor activities.Travellers can expect amenities such as spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces that provide stunning views of the surrounding nature.
Are there pet-friendly house rentals in Ossipee?
In Ossipee, New Hampshire, there are several pet-friendly house rentals available, ideal for travellers looking to enjoy the beautiful natural surroundings with their furry companions. Many of these properties come equipped with amenities such as spacious living areas, fully stocked kitchens, and outdoor spaces, including decks or patios where you can relax and enjoy the fresh air.The area offers a wealth of outdoor activities, with nearby lakes and hiking trails great for pet owners. Ossipee Lake, in particular, provides opportunities for swimming, boating, and exploring the scenic beauty of the region. Additionally, the surrounding forests are ideal for walks and adventures with your pets, making this location a fantastic choice for those seeking a pet-friendly getaway.
Are there any remote work holiday rentals in Ossipee?
In Ossipee, New Hampshire, there are approximately 18 holiday rentals suitable for remote work. This picturesque area, known for its scenic lakes and mountains, provides a tranquil backdrop for those looking to work away from home. Many of the properties offer reliable Wi-Fi, ensuring connectivity for work-related tasks.Travellers can expect a variety of amenities, including spacious living areas, fully equipped kitchens for convenient meal prep, and sometimes even outdoor spaces for a refreshing break. The vicinity to local attractions such as Ossipee Lake and the surrounding White Mountains offers opportunities for outdoor activities, making it an ideal location for balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Ossipee?
In Ossipee, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals, and decks or patios where they can enjoy the natural surroundings. Onsite parking is also available, making it convenient for visitors travelling by car. Many properties feature porches or lanais, superb for relaxing outdoors, and some even come equipped with blenders for those who enjoy making smoothies or other blended beverages.
When is the best time to visit Ossipee for a holiday rental?
The peak season for visiting Ossipee is from June to August, with July being the most popular month. This vibrant time attracts families and outdoor enthusiasts who flock to enjoy the region's stunning lakes, hiking trails, and various water sports. With temperatures typically ranging from 20 to 30 degrees Celsius, it's great for swimming, kayaking, and soaking up the sun.During the summer months, the area buzzes with activity, offering opportunities for sightseeing and relaxation. Visitors can explore the beautiful Ossipee Lake, embark on scenic hikes, or simply unwind in one of the charming holiday rentals that dot the landscape. The warm weather and lively option make this a prime time for creating memorable experiences with family and friends.If you're looking for a more budget-friendly option, consider visiting in December. While the temperatures drop to around -5 to 5 degrees Celsius, this month offers a unique charm with fewer crowds and the chance to enjoy winter activities, such as snowshoeing or cosy evenings by the fire in your holiday rental.
What are the top attractions in Ossipee?
In Ossipee, New Hampshire, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The Ossipee Lake, a central feature of the region, offers opportunities for swimming, boating, and fishing, making it a lovely spot for water enthusiasts. Nearby, the scenic Ossipee Mountains provide excellent hiking trails, such as those leading to the summit of Mount Shaw, which rewards hikers with stunning views of the surrounding landscape.For those interested in winter sports, the area provides access to several ski resorts, including King Pine Ski Area, which is superb for families and offers a range of slopes for different skill levels. Additionally, the quaint town centre features local shops and restaurants where visitors can experience the charm of New Hampshire's small-town vibe. The annual Ossipee Valley Music Festival is also a highlight for those visiting in the summer, showcasing local talent and fostering a sense of community.
Are all fees included in the Ossipee holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Ossipee holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Ossipee with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Ossipee holiday homes?
You can find great discounts on holiday homes in Ossipee on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Ossipee holiday home booking on Bookabach?
To find Ossipee holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Ossipee?
A long-stay holiday home in Ossipee is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Ossipee holiday home?
Book your Ossipee holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Ossipee?
Prices for holiday homes in Ossipee vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Ossipee to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.