Vacation rentals in Ossipee

4.9 out of 5 average rating, 107 reviews

A spacious chalet is nestled in a wooded setting, featuring a symmetrical facade with large windows that invite natural light. An expansive deck extends along one side, offering outdoor space. The exterior is clad in light-colored siding, surrounded by lush greenery.

Chalet in Tamworth

Rustic Mountainside Chalet

Located on a wooded mountainside in the White Mountains & the Lakes Region of NH, close to hiking, 5 minutes to the rivers and 15 minutes to Lake Chocorua and Lake Ossipee for swimming/kayaking/tubing or just relax and enjoy the views of the mountains. Peaceful Chalet with one bedroom with one bunk bed unit with queen mattresses, and a large master bedroom loft with Cali King, kitchen, and 2 x bathrooms, a deep jetted tub. The basement is converted into an in-law’s suite where my parents live.

5 out of 5 average rating, 12 reviews

A two-story vacation home is surrounded by lush greenery, featuring large windows that allow light to fill the interior. A circular arrangement of red Adirondack chairs encircles a fire pit in the foreground, creating a welcoming outdoor gathering space. An American flag and seasonal decorations are displayed on the deck.

Home in Ossipee

The Tinker Bell on Ossipee Lake

Our Ossipee Lake vacation home is a wonderful all-seasons property, – excellent for a summer vacation, a fall foliage trip, or as a winter skiing/snowmobiling destination. This home is the perfect ‘basecamp’ from which to explore the Lakes region & Mt. Washington Valley. With 5 BRs and 3 full baths in the main house and adjacent, seasonal “guest cottage” this home is perfect for extended family vacations or other groups. You'll love the breathtaking views of the lake and the White Mountains!

4.79 out of 5 average rating, 494 reviews

A serene view of a lake surrounded by trees, reflecting the clear blue sky. The water's surface appears smooth, indicating calm conditions. The landscape features distant houses among the trees, contributing to a peaceful natural setting.

Cottage in Freedom

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

4.87 out of 5 average rating, 410 reviews

A bright living space showcases a comfortable gray sofa with a red throw, a wooden coffee table, and a patterned rug. A small kitchenette with white cabinetry and a dining area is visible, along with a lofted sleeping area in the background.

Apartment in Porter

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

4.9 out of 5 average rating, 91 reviews

The warm interior features a cozy seating area with wicker chairs and a small table beside a wood stove. Light filters through large windows adorned with checkered curtains, and rustic wooden beams enhance the cabin's charm. A patterned area rug complements the wood flooring.

Cabin in Ossipee

Cozy Cabin Retreat just off Lake Ossipee

Nestled on 17 acres and backed by 400 acres of Ossipee Forest just off Lake Ossipee, this cabin is perfect for a quiet retreat or a home base for all the splendor NH has to offer. Sit by the fire with your favorite book and beverage or cook your favorite meal in the full kitchen. The wrap around screened in porch is a great place to enjoy company or stare off into the woods looking for wildlife to wander by. No matter the season this cabin is close to all your favorite outdoor activities.

4.98 out of 5 average rating, 101 reviews

The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.

Apartment in Wakefield

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

4.76 out of 5 average rating, 58 reviews

A living room is featured with a gray sofa adorned with blue cushions. A wooden coffee table sits on a beige rug, while a small side table is positioned nearby. A cozy armchair offers additional seating, and light streams through the windows adorned with patterned curtains.

Cottage in Ossipee

Hear the stream from bed.

Take it easy at this quiet getaway in the woods. Hearing the sound of the water from bed is all the peace you will need. The kitchen is stocked with basic cooking supplies and spices. If going out to eat is your vibe, there are local restaurants within a 10 minute drive. The house has all hardwood floors two bedrooms, office, living room, kitchen, sun room and off-street parking. Many delicious year round restaurants, shopping and endless outdoor activities within 10/30mins.

5 out of 5 average rating, 119 reviews

A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.

Guesthouse in Hiram

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

4.99 out of 5 average rating, 111 reviews

A charming red cabin is set amidst towering pine trees, featuring a spacious wooden deck that wraps around the front. The façade showcases large windows that invite natural light, and a welcoming entryway leads inside.

Cabin in West Ossipee

Cluck's Cabin-Lakes/Mt Wash Valley

Adorable, obsessively clean, Cabin set in the Lakes Region and Mount Washington Valley. Set on almost 2 acres, you'll have a view of the mountains and wooded meadow that changes by the minute. Huge wrap around deck, firepit under the stars. Great Hospitality! Short stays available Thinking about two or more nights over Veteran's Day Weekend? Please inquire - discount available We offer early check in / late check out as often as possible. Let's discuss when you inquire.

4.9 out of 5 average rating, 104 reviews

The exterior of the spacious home presents a blend of stone and siding, surrounded by lush greenery. A paved driveway leads to the entrance, while the colorful sunset casts a warm glow across the landscape.

Home in Freedom

Our Mountain Retreat – Lake Ossipee Access

Spacious 5 bedroom home with convenient lake access, just a short walk or 5-minute drive to beautiful Lake Ossipee. Enjoy easy proximity to King Pine Ski Area and a quick 25-minute drive to Conway, where you'll find outlet shopping, scenic hiking trails, and a variety of restaurants. This property features a large yard with a fire pit, and a hot tub for ultimate relaxation. The master bedroom includes a private deck—perfect for morning coffee or stargazing at night.

4.93 out of 5 average rating, 205 reviews

A cozy nook features a vibrant blue futon with decorative throw pillows, beneath colorful string lights. A wooden stool offers a rustic touch, paired with two wooden chairs. Natural light enters through a large window, illuminating the relaxing atmosphere.

Cottage in Tamworth

*Amazing Reviews! *Private Yard *Outdoor Shower!

This guesthouse located in the beautiful & historic Tamworth/Chocorua New Hampshire. This house has many special areas to just relax & enjoy nature and the peacefulness this area of the world has to offer! Travel inspired & colorful! You will love both the front and back patios one with a grill & gazebo for outdoor dining in any weather & nicely lit at night & the other with a great porch and fire pit area. The outdoor shower off the porch is just AMAZING!

4.87 out of 5 average rating, 463 reviews

The living area features high wooden ceilings and large windows, allowing natural light to fill the space. A comfortable couch is positioned near the windows, while a television is mounted on the opposite wall. The warm wooden flooring complements the rustic design.

Guesthouse in Brownfield

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Ossipee vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Ossipee

4.96 out of 5 average rating, 25 reviews

A wooden deck showcases a small round table paired with two chairs, softly illuminated by string lights. The view features a serene landscape of trees and a reflective water surface, creating a peaceful ambiance at dusk.

Guest suite in Madison

Crisp Mornings + Warm Days in the White Mountains

5 out of 5 average rating, 26 reviews

A cozy living area features light-colored sofas accented with black and white throw pillows. Black ottomans provide additional seating or a place to rest items. The open layout connects the living space to a well-equipped kitchen in the background, with wooden cabinets and a visible dining area.

Home in Freedom

Cozy 3-bdrm - Ossipee Lake access, Ski, Shop, Hike

Guest suite in Tuftonboro

A comfortable living area features a dark sofa adorned with decorative pillows. Two light armchairs provide additional seating, and a coffee table sits on a patterned area rug. The compact kitchen includes a refrigerator and microwave, with washer and dryer units discreetly located nearby.

5 out of 5 average rating, 64 reviews

New-Adorable Spacious "Garden Cape" Guest Suite

4.89 out of 5 average rating, 61 reviews

A spacious home is shown framed by trees, showcasing a large deck and a screened-in porch. In the foreground, several light blue chairs are arranged around a fire pit, surrounded by a grassy area and enhancing the outdoor gathering space.

Home in Ossipee

Spacious, renovated 2-bedroom home on golf course!

5 out of 5 average rating, 23 reviews

A serene view of Mirror Lake presents a tranquil morning scene, where mist rises gently from the water's surface. Two chairs are positioned in the foreground, inviting relaxation. Soft sunlight glimmers on the lake, enhancing the peaceful ambiance of the natural surroundings.

Home in Tuftonboro

Peaceful Lakefront Retreat

4.93 out of 5 average rating, 59 reviews

A cozy interior features a queen-size bed draped in a yellow coverlet, complemented by dark cushions. Natural light filters through patterned curtains, while decorative touches, such as a wall art piece and potted plants, enhance the inviting ambiance.

Tiny home in Tamworth

The River Nook - Tiny Cozy Boho Home

Place to stay in Shapleigh

A charming red schoolhouse, dating back to 1866, is surrounded by tall trees and a well-kept grassy area. The structure features white trim, large entrance doors, and a bell tower, evoking a sense of history and nostalgia.

5 out of 5 average rating, 91 reviews

Historic Schoolhouse c1866 / Pets OK / Hot tub