Holiday rentals in Ossipee

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Top-rated holiday rentals in Ossipee

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Guest favourite

Chalet in Madison

4.97 out of 5 average rating, 114 reviews

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!

Top guest favourite

Tiny home in Wentworth

4.99 out of 5 average rating, 154 reviews

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

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!

Top guest favourite

Farm stay in Alton

4.99 out of 5 average rating, 412 reviews

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

Guest favourite

Cabin in Ossipee

5 out of 5 average rating, 16 reviews

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.

Guest favourite

Chalet in Tamworth

4.89 out of 5 average rating, 100 reviews

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.

Guest favourite

Cottage in Tamworth

4.95 out of 5 average rating, 120 reviews

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

Guest favourite

Guest suite in Wolfeboro

4.87 out of 5 average rating, 158 reviews

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!

Guest favourite

Flat in Porter

4.87 out of 5 average rating, 395 reviews

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.

Guest favourite

Home in Albany

4.83 out of 5 average rating, 460 reviews

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!

Guest favourite

Cabin in Conway

4.95 out of 5 average rating, 163 reviews

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.

Top guest favourite

Cabin in West Ossipee

4.99 out of 5 average rating, 108 reviews

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.