Cottage holiday rentals in Ossipee

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Top-rated cottage rentals in Ossipee

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Top Guest favourite
The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.
Cottage in Wakefield
4.99 out of 5 average rating, 104 reviews

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

Top Guest favourite
An inviting loft bedroom is featured, featuring a spacious bed with a light-colored coverlet. Natural wood walls and ceiling create a warm ambiance. A colorful peacock rug adds a unique touch, while windows provide pleasant lighting. A fan hangs overhead, contributing to airflow.
Cottage in Tamworth
4.94 out of 5 average rating, 219 reviews

*5-Star CLEAN *Outdoor Shower *Private Yard & FUN!

This guesthouse is located in the beautiful and historic areas of Tamworth & Chocorua, NH. It features many inviting spaces where you can relax and enjoy the natural beauty & peaceful surroundings. The decor is travel-inspired and vibrant, creating a warm & fun atmosphere. You will love the two patios: one includes a grill and gazebo for outdoor dining, comfortably lit for evening use, while the other boasts a lovely porch and a fire pit area. The outdoor shower off the porch is truly amazing!

Top Guest favourite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood
4.94 out of 5 average rating, 134 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided

Guest favourite
The custom log home is surrounded by lush greenery, showcasing a wrap-around deck with multiple seating areas. A hammock is positioned in the foreground, inviting relaxation. The sloped driveway leads to the entrance, enhancing the natural, tranquil setting.
Cottage in Meredith
4.86 out of 5 average rating, 208 reviews

Log Home Meredith NH Pet Friendly Custom Fire-Pit

Log home getaway in Meredith NH, near Lake Winnipesaukee! 4-night minimum in July & August 3-night minimum on holiday weekends 2-night minimum in the off-season Enjoy a peaceful stay in our cozy custom log home —just down the road from Lake Winnipesaukee! Our home offers a wraparound deck, outdoor fire pit, and is pet-friendly for up to two dogs. Only 3 miles to downtown Meredith, close to beaches, hiking, restaurants, spas, and breweries. Perfect for a relaxing escape with family and friends.

Top Guest favourite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton
4.99 out of 5 average rating, 169 reviews

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

Top Guest favourite
A sleek black stove is set against a rustic brick wall, featuring a glowing flame that provides warmth. In the foreground, softly blurred decorative ornaments hint at a holiday theme, while a patterned rug adds comfort to the inviting space.
Cottage in Wolfeboro
4.96 out of 5 average rating, 130 reviews

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… your spot for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk from the property you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine!

Top Guest favourite
A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.
Cottage in Middleton
4.97 out of 5 average rating, 169 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Superhost
A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.
Cottage in Parsonsfield
4.86 out of 5 average rating, 181 reviews

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Top Guest favourite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton
4.96 out of 5 average rating, 226 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Top Guest favourite
A serene lake view is framed by trees adorned with autumn foliage. The calm water reflects the vibrant colors of the leaves, while a wooden platform is visible on the lake's surface. The scene suggests a tranquil and peaceful retreat.
Cottage in Gilmanton
4.97 out of 5 average rating, 123 reviews

Private Beach, Lake Front, Family Friendly Cottage

Our clean private sandy beach, with a gentle slope is perfect for all swimmers. Sawyer Lake is a fun community. Enjoy our fun lakefront cottage with the perfect layout. 15 min. to Gunstock, Weirs Beach & Tilton Outlets • Kids will want to stay downstairs with a walkout, Foosball table, board games, TV, and 2 gaming systems [XBox 360° & Wii] with games. • Adults relax in peace upstairs with 2 private bedrooms, living area, & wood burning fireplace. Ask about weekends.

Top Guest favourite
A cozy cottage is framed by lush greenery and colorful landscaping, featuring a welcoming front porch and a sunroom with large windows. A picnic table is positioned nearby, inviting outdoor relaxation. The property is set against a backdrop of trees, contributing to a private and serene environment.
Cottage in Brownfield
4.99 out of 5 average rating, 285 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Top Guest favourite
The lake-front cottage is surrounded by trees and features a spacious deck with seating. Colorful adirondack chairs are arranged in a circular pattern near a stone-bordered landscaping area, adding inviting outdoor space for relaxation. A screen porch is visible on the side of the house.
Cottage in Middleton
4.98 out of 5 average rating, 112 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.

Popular amenities for Ossipee cottage rentals

Quick stats about cottage rentals in Ossipee

  • Total holiday rentals

    Explore 10 holiday rentals in Ossipee

  • Nightly prices starting at

    Ossipee holiday rentals start at $111 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,100 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Wi-Fi availability

    10 of Ossipee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Ossipee rentals

  • 4.8 Average rating

    Ossipee stays are highly rated by guests—averaging 4.8 out of 5!