Vacation rentals in Ossipee

4.97 out of 5 average rating, 114 reviews

A wooden walkway leads to the entrance of a chalet, framed by trees displaying fall colors. The mountain scenery in the background reveals rolling hills under a partly cloudy sky, enhancing the sense of elevation and connection with nature.

Chalet in Madison

Breathtaking mountain views - Hidden gem!

Chalet in the Clouds!⛅️ Relax & Rejuvenate w/ panoramic views of White Mountains from any of the 4 decks of Kailaśa Chalet! Perched on top of a mountain overlooking Mt Chocorua & Silver Lake w/ majestic views of Mt Washington Valley. So easy to get lost in the beauty of Kailaśa! Wake up to the experience of being above the clouds overlooking the valley! Settle down after dinner around the stone fireplace while watching your favorite shows on 65" TV It's not just a rental it's an experience!

4.99 out of 5 average rating, 154 reviews

The A-frame cabin is partially obscured by tall trees, with a dark exterior and a striking green door. Snow blankets the ground, and a couple of wooden chairs are positioned on the porch, inviting relaxation in a serene, wooded setting.

Tiny home in Wentworth

Tiny Riverfront A-Frame w/ Mountain Views, Hot Tub

Welcome to 'The Alexander' @ Casa de Moraga! This tiny A-frame is nestled on the bank of Baker River w/ breathtaking views of the river & White Mountains. Full kitchen, bathroom w/ shower & living/dining area. Wake up in the loft bedroom & see the mountains & river from bed. Read on the couch & enjoy the gel fuel fireplace, take a swim or fish in the river - relax in your private hot tub on the deck overlooking the river! 10 min to Tenney MTN. 35 min to Ice Castles, Franconia, Loon & Waterville!

Superhost

Two sheep stand closely together in a sunlit farmyard. One sheep has a thick black coat, while the other is grey and white. In the background, a brown cow grazes peacefully, framed by trees and a fenced area.

Home in Wolfeboro

4.88 out of 5 average rating, 205 reviews

Mountain Views & Animals near Winnipesaukee!

Wolfeboro 260 year old farm! Enjoy private 3 bd 2 bth incl. linens, towels and a full kitchen with pots/pans and utensils. Plenty of room for whole family or multiple couples! Enjoy hiking, skiing, swimming, boating, historic sites, museums and much more. The beautiful lakes region offers endless fun activities for every season! Only 7 min away is everything you need grocery, gas, pharmacy, and coffee. Enjoy farm life without hard work! Donkeys, alpacas, sheep, and more! Baby goats & puppies!

4.99 out of 5 average rating, 412 reviews

A spacious outdoor area is visible from a wooden deck, framed by vibrant autumn leaves. The landscape features lush green grass and distant rolling hills, providing a serene backdrop. A small shed is positioned on the left, blending harmoniously into the natural surroundings.

Farm stay in Alton

Treehouse Penthouse ❤ Beautiful inside & out

Kick back and relax in this calm, stylish apartment space. This space is an open concept with a king size bed. Lots of windows bring in natural light, cathedral ceiling and amazing view! A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have your own space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

5 out of 5 average rating, 16 reviews

A living area features a full-size couch and a recliner, positioned around a coffee table atop a colorful area rug. A flat-screen TV is mounted on the wall, with a view into the kitchen area visible in the background. Natural light enters through a window, highlighting the cozy ambiance.

Cabin in Ossipee

Cozy Mountain Cabin for Quiet Getaway

Welcome to our Ossipee cabin! It's the perfect space for a relaxing vacation away from the hustle and bustle. Located on a quiet street, you have access to various attractions within a short distance. You can enjoy public swimming at nearby Conner Pond, there are many close by hiking trails, including Bayle Mtn or Chocorua, improve your golf game at Indian Mound Golf Club, hit the slopes at King Pine Ski Area, visit the shops/restaurants in North Conway and end your day sitting by the fire-pit.

4.89 out of 5 average rating, 100 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.

4.95 out of 5 average rating, 120 reviews

The exterior of the house features a combination of timber frame siding with a light-colored front and dark wood accents. A grassy area is present, surrounded by lush greenery and orange flowers. A hammock is seen in the yard, creating a peaceful outdoor space.

Cottage in Tamworth

5*Clean! *Private patio *Sleeps 6 *Outdoor Shower!

This home has many unique areas to unwind inside & out! *Private sunken patio fully equipped with a LP/charcoal grill *Firepit *Covered outside dining *Lounge chairs *2-Hammocks *OUTDOOR SHOWER! *Sunporch *Private driveway *Quiet tucked away yard surrounded by nature! *Close to many Hikes & Wedding venues. 'The Corner House', a timber frame cape, is perfect for a New England getaway. The house consists of a re-located1820's post & beam frame and is great place to gather with family & friends

4.87 out of 5 average rating, 158 reviews

A bedroom features a spacious bed dressed in neutral linens, complemented by a decorative pillow. A nightstand holds a lamp with a soft light. Natural light filters through vertical blinds, enhancing the serene atmosphere. A framed black-and-white photograph reflects a peaceful lake scene.

Guest suite in Wolfeboro

Downtown, Cozy, Cute, and Convenient!

Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

4.87 out of 5 average rating, 395 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.

4.83 out of 5 average rating, 460 reviews

A compact kitchen area is shown, featuring a full-size refrigerator, stove, and sink with countertop space. Cabinets are installed above and below the counter. A cozy futon couch is positioned in the foreground, complementing the warm wooden paneling on the walls.

Home in Albany

Cozy Guest Suite in White Mountain National Forest

Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

4.95 out of 5 average rating, 163 reviews

A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.

Cabin in Conway

The Conscious Cabin

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

4.99 out of 5 average rating, 108 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.

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

Superhost

A serene river scene is depicted, where calm waters reveal a sandy bottom, illuminated by sunlight. Lush green trees frame the setting, and two kayaks are anchored nearby, partially obscured by the surrounding foliage. The tranquil environment invites relaxation and exploration.

5 out of 5 average rating, 12 reviews

Waterfront cottage on Bearcamp River in OssipeeNH

4.88 out of 5 average rating, 60 reviews

The spacious studio guesthouse features a large queen bed with decorative pillows and a cozy daybed with a trundle. Natural light enters through multiple windows, illuminating a vibrant area rug and a wooden table against a backdrop of exposed beams.

Guesthouse in Freedom

Beautiful & Relaxing Retreat Close to Ossipee Lake

5 out of 5 average rating, 49 reviews

A white horse stands calmly behind a white wooden fence, with verdant green grass surrounding it. The background consists of lush trees, contributing to a serene rural landscape. Soft sunlight illuminates the scene, highlighting the horse's graceful form.

Guesthouse in Wakefield

Peaceful Summer Retreat: Private Horse Farm

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.

5 out of 5 average rating, 10 reviews

The Tinker Bell on Ossipee Lake

5 out of 5 average rating, 40 reviews

A serene lakefront scene captures a wooden dock extending into calm waters, reflecting vibrant orange and pink hues of a sunset. Silhouettes of trees and a distant hill frame the tranquil setting, creating a peaceful atmosphere for relaxation.

Cottage in Ossipee

Peaceful Ossipee Lake Cottage Private Beach/Dock

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.

4.9 out of 5 average rating, 58 reviews

Spacious, renovated 2-bedroom home on golf course!

4.93 out of 5 average rating, 73 reviews

A scenic view of Lake Ossipee is captured, featuring calm waters reflecting a clear blue sky. Lush green grass surrounds the area, complemented by carefully landscaped shrubs and a single tree displaying autumn colors. The backdrop reveals distant mountains under bright, open skies.

Condo in Ossipee

Ossipee Lake Waterfront Condo

Superhost

A comfortable living area is presented, featuring a large sectional sofa, armchair, and a wooden coffee table at its center. Natural light filters through multiple windows, enhancing the welcoming ambiance. A stone fireplace is visible, adding a cozy element to the space.