Cottage vacation rentals in Ossipee

4.99 out of 5 average rating, 103 reviews

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

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.

4.96 out of 5 average rating, 135 reviews

Cottage in Tamworth

Amazing Reviews! 5*Clean! Big Patio-Outdoor Shower

This cottage 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

4.97 out of 5 average rating, 160 reviews

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Off-Season Escape Nestled just next door to Ferris Farm, our family-run flower farm, this charming cottage offers the perfect private space to rest and recharge. Even as the gardens rest for winter, there’s beauty all around. Stay in and enjoy slow, coffee-filled mornings, quiet walks around the property, and cozy, starlit evenings by the fire pit. Or take a drive and explore Portland’s diverse food scene. Perfect for a romantic retreat, solo escape, or remote work getaway.

4.96 out of 5 average rating, 121 reviews

The welcoming living area features a comfortable navy sofa, adorned with a light-colored throw pillow. A wooden coffee table displays a potted plant. The kitchen is visible in the background, equipped with modern appliances, while artwork depicting animals is mounted on the walls.

Cottage in Bartlett

Lazy Bear Cottage-Rustic & Peaceful Winter Retreat

Experience rustic charm at our lovely Bartlett property-perfectly situated to be a year-round oasis! Only a mile to Attitash and under 30 min to 5 other ski resorts! In the summer your backyard is the Saco river with hundreds of trailheads minutes away! For foliage, 2 miles to Bear Notch and the Kanc - the best starting point! Seeking serenity? Spring it is! Enjoy the valley without the high season craze. With a fenced yard for your pups and the comforts of N. Conway nearby, it can't be beat!

4.99 out of 5 average rating, 157 reviews

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

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake. Swing in the hammock while listening to the cry of the loons. Or enjoy your morning coffee overlooking the quiet cove from your covered porch. 100 feet of shoreline in the calm 3rd basin of the lake. This entire basin is a "no-wake" zone which allows safe swimming for the whole family. Enjoy fishing, search for turtles, or explore beyond the cove using the canoe, kayaks, or paddle boards. Dock your own boat at the 24' aluminum dock.

4.87 out of 5 average rating, 168 reviews

The two-story cottage features a mix of wooden siding and a gabled roof. Surrounded by greenery, it includes a raised deck accessible by stairs at the front. A fire pit is visible nearby, with a rustic fence marking the perimeter of the yard.

Cottage in Woodstock

A: Cozy 2-BR Cottage Duplex - Unit A

Cozy, quirky, and very convenient! Welcome to our humble, pet friendly cottage in the White Mountains. This unique cottage duplex is our home base for hiking, skiing, and paddling, and we're happy to share it with you! Tucked away on the edge of the village of North Woodstock, our modest retreat is a stones throw from all the excitement the region has to offer. Take a short walk to the nearest swimming hole, explore the National Forest, and be back in time to enjoy dinner on the back deck!

4.89 out of 5 average rating, 258 reviews

The exterior of Pebble Cottage is shown, featuring a charming yellow facade with a welcoming front porch. Two large windows adorned with flower boxes are displayed, offering a glimpse of the landscaped yard framed by a white picket fence.

Cottage in Bridgton

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a hammock, very quiet retreat. Please note it's old!

4.97 out of 5 average rating, 168 reviews

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

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.

4.86 out of 5 average rating, 175 reviews

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

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.

4.96 out of 5 average rating, 123 reviews

The sandy beach area features several white adirondack chairs arranged for relaxation. Gentle waves lap at the shoreline, where boats are anchored in the distance. A staircase leads up from the beach to a grassy area, surrounded by trees, under a clear sky.

Cottage in Wolfeboro

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… Here is your chance 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 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.

4.99 out of 5 average rating, 272 reviews

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

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.

4.96 out of 5 average rating, 205 reviews

The hot tub is filled with bubbling water, positioned to capture views of the frozen lake and sunset hues in the sky. Surrounding scenery includes a winter landscape, with trees lining the shore and a distant dock. Gentle waves are visible on the water's surface.

Cottage in Middleton

☀ 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!

Popular amenities for Ossipee cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.98 out of 5 average rating, 47 reviews

A charming cottage is viewed from the front, featuring a red roof and stone chimney. Surrounding greenery includes lush trees and colorful flowers. A gravel path leads to the entrance, highlighted by welcoming steps and a well-maintained landscape.

Cottage in Jackson

Charming Quiet Cottage close to hiking & JXN Falls

4.71 out of 5 average rating, 52 reviews

The exterior of a charming yellow cottage is presented, with white trim surrounding inviting windows. A well-maintained pathway of pavers leads to the entrance, flanked by green shrubs and small plants. Tall trees provide a natural backdrop, enhancing the serene atmosphere.

Cottage in Wells

Cottage 225 "Beach House"

4.92 out of 5 average rating, 143 reviews

The exterior of the cottage features a welcoming wooden deck with a railing, surrounded by trees. Light filters through the leaves, casting shadows on the ground. The building showcases a simple yet functional design with multiple windows reflecting the serene woodland setting.

Cottage in Norway

Cottage with Whirlpool tub - McLeod

A well-lit bedroom featuring a wooden bed with soft bedding. A ceiling fan provides airflow, while natural light filters through a nearby window. A mirror and a decorative lamp complement the cozy atmosphere of the space.

4.82 out of 5 average rating, 67 reviews

Cozy Cottage on a Lake, near Gunstock Mountain

5 out of 5 average rating, 27 reviews

Cottage in Shapleigh

Quaint New England Cottage in the Pines | Lakeside

The living area features a brown leather sofa paired with a decorative throw, surrounded by large windows that invite natural light. A textured area rug lies beneath a low coffee table, with decorative objects and plants adding a touch of greenery.

4.87 out of 5 average rating, 115 reviews

Close to skiing, hot tub, beach access & fire pit

5 out of 5 average rating, 73 reviews

Cottage in Wells

Cozy Cottage Minutes from Ogunquit

4.96 out of 5 average rating, 114 reviews

A screened-in porch features a sectional sofa surrounding a glass-top table, providing a comfortable seating area. Large windows offer views of the surrounding trees, allowing natural light to fill the space. A fireplace adds a focal point, enhancing the cozy retreat atmosphere.

Cottage in Northwood

The Loon Nest, Waterfront Lake House, Wood Hot Tub

Pet-friendly cottage rentals

4.98 out of 5 average rating, 81 reviews

The exterior of the cottage features a wooden structure with large windows framed in green. A sliding glass door leads to a spacious deck area, where two pink chairs are positioned invitingly. A picnic table and a black grill can be seen on the deck.

Cottage in Madison

Welcome to Lakota! A Cozy 2 BR Cottage.

4.93 out of 5 average rating, 137 reviews

A renovated home features a white exterior with green trim, set against a backdrop of vibrant autumn foliage. A large boulder is positioned near the front of the house, and the well-maintained lawn adds to the charming rural setting.

Cottage in Bethlehem

Cozy Cottage in White Mountains Bethlehem, NH

4.89 out of 5 average rating, 61 reviews

A welcoming living room features a spacious sofa adorned with decorative pillows. A coffee table sits at the center, surrounded by various seating options including a light-colored armchair and a staircase leading to an upper level. Natural light filters in through windows, accentuating the wood-paneled ceiling.

Cottage in Ossipee

5 Bedroom Cottage overlooking Ossipee Lake

A cozy seating area is arranged on a screened-in porch, featuring comfortable sofas adorned with floral pillows. A wooden table is set with two potted plants and decorative lanterns, while a patterned area rug adds texture to the space.

4.89 out of 5 average rating, 109 reviews

Sawyer Lake Bear House

4.93 out of 5 average rating, 95 reviews

A fire pit surrounded by six gray Adirondack chairs sits in a grassy area, with a stone ring enclosing a bright flame. The cottage is visible in the background, featuring a spacious deck and lush green trees creating a serene natural setting.

Cottage in Gilford

Cozy, Pet-Friendly Escape Near Lake & Mountains

A sandy beach area is depicted where four individuals sit along the water's edge, engaging with the lake. A small boat is moored nearby, and a floating platform is visible on the water's surface. Gentle waves lap at the shore, creating a serene atmosphere.

4.97 out of 5 average rating, 123 reviews

Private Beach, Lake Front, Family Friendly Cottage

4.91 out of 5 average rating, 53 reviews

A charming home nestled among trees, with a spacious deck extending from the front. Large windows offer views of the serene surroundings, while a pathway leads from the house to the water's edge. The exterior features a mix of natural elements and a carefully maintained yard.

Cottage in Raymond

The Great Escape - Picturesque Sebago Lake

Cottage in Center Ossipee

A cozy living area features a comfortable seating arrangement with two sofas, a ceiling fan, and a large television mounted on the wall. Natural light enters through a nearby door, illuminating the wooden accents and floor. A wood-burning stove adds warmth to the space.

4.7 out of 5 average rating, 60 reviews

Charming White Mountain Escape Free Early Check-in

Private cottage rentals

4.94 out of 5 average rating, 69 reviews

The cottage features a striking red exterior with an A-frame design and a welcoming front door. A gas grill is positioned on the deck, surrounded by lush greenery and a decorative lattice. Mature trees provide shade, complementing the inviting setting.

Cottage in Campton

Red Sleigh Chalet #11 - Rustic Cabin by the Pemi

4.85 out of 5 average rating, 13 reviews

Cottage in Shapleigh

Family & Pet Friendly, Lakefront Home

4.89 out of 5 average rating, 46 reviews

A charming cottage is nestled among trees, showcasing a rustic red exterior with white trimmings. Air conditioning units are positioned in the windows, and an American flag hangs by the entrance. A wooden ramp provides access to the porch, leading to a welcoming front entry.

Cottage in Conway

Pet Friendly North Conway Cottage

5 out of 5 average rating, 64 reviews

A charming cottage exterior is presented, featuring a white clapboard façade and a welcoming front door painted in soft pink. Two large windows are adorned with brown shutters, while flower boxes sit beneath each window, enhancing the serene appearance of the home.

Cottage in Kennebunk

*River Rose Cottage* River I Tub I Fireplace

5 out of 5 average rating, 32 reviews

A well-maintained lawn extends toward a tranquil lake, framed by lush trees. A wooden deck is visible in the foreground, leading to seating areas by the water's edge. The serene landscape captures the essence of a peaceful lakeside retreat.

Cottage in Suissevale

Year-round Cottage located on Lake Winnipesaukee

5 out of 5 average rating, 17 reviews

A private dock extends into calm waters, featuring a small table and two lounge chairs beneath a vibrant red umbrella. Surrounding trees create a serene backdrop, with autumn leaves scattered across the wooden deck.

Cottage in Shapleigh

Serene Lakefront Retreat in Southern Maine

5 out of 5 average rating, 48 reviews

A quaint outdoor seating area features four white Adirondack chairs arranged around a central fire pit. The space is framed by trees, creating a serene view of the water and a nearby dock. A large deck is visible in the background.

Cottage in Alton

Windswept Cottage: A Winnipesaukee Waterfront