Cottage holiday rentals in Ossipee

4.99 out of 5 average rating, 104 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.

4.97 out of 5 average rating, 161 reviews

Cottage in Buxton

Peaceful Cottage on Maine Flower Farm

Maine’s Peaceful Off-Season Escape Nestled next door to Ferris Farm, our family-run flower farm, this charming cottage offers a private place to rest and recharge. Enjoy slow, coffee-filled mornings, quiet walks, and cozy evenings by the fire pit. Use the cottage as your home base to explore nearby beaches (30 minutes) or head into Portland (35 minutes) for breweries, coffee shops, and great dining. Perfect for a couple retreat, solo escape, or remote work getaway, with dedicated workspace.

4.96 out of 5 average rating, 134 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!

4.87 out of 5 average rating, 174 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!

4.91 out of 5 average rating, 420 reviews

A charming historic house is surrounded by mature trees, showcasing a white exterior and a welcoming front porch with rocking chairs. A well-maintained picket fence frames the property, while colorful flower arrangements are seen near the windows, enhancing the peaceful outdoor setting.

Cottage in Plymouth

Plymouth's Historic Doll House; A tiny house

The Doll House has everything you’ll need at under 700 square feet. This fully-outfitted, historic, full-house rental has a complete kitchen, living room, two-bedrooms, bath, back sitting room, front farmer's porch and beautiful gardens and sitting areas. The Doll House is within easy walking distance to the Town Common, great restaurants and shopping, the Flying Monkey, and PSU. We are just a few minutes' drive to the Barn on the Pemi and Holderness School. NH Rooms Tax; License #059528.

4.89 out of 5 average rating, 266 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!

4.99 out of 5 average rating, 164 reviews

Cottage in Acton

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!

4.96 out of 5 average rating, 127 reviews

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

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!

4.86 out of 5 average rating, 180 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, 214 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. The sunsets can be unbelievable!

4.95 out of 5 average rating, 146 reviews

A spacious living area features oversized leather furniture arranged around a coffee table. The well-equipped kitchen is visible in the background, highlighted by warm wooden cabinetry and modern appliances. A cozy fireplace adds an inviting touch, with soft lighting enhancing the overall ambiance.

Cottage in Conway

Cozy Cottage close to town and area attractions

Welcome to our family cottage located minutes from everything the valley has to offer! Three miles from main street North Conway. All outdoor activities the valley offers only a short drive away! Well-appointed home offering all you will need on your getaway no matter the season. Relax and watch a movie on the oversized leather couches, play pool and watch a game in the basement bar area, or sleep in on our luxury mattresses and bedding. You will not be disappointed!!

4.99 out of 5 average rating, 280 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.

Popular amenities for cottage rentals in Ossipee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.83 out of 5 average rating, 71 reviews

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.

Cottage in Gilmanton

Cozy Cottage on a Lake, near Gunstock Mountain

5 out of 5 average rating, 31 reviews

Cottage in Shapleigh

Cottage in the Pines | Lakeside + Sauna + Hot Tub

5 out of 5 average rating, 77 reviews

Paradise Found Minutes from Ogunquit | Heated Pool

The cottage exterior features a welcoming entrance with a wooden porch and steps leading to a pink door. Large windows framed in white allow natural light to fill the space, surrounded by well-maintained landscaping with green grass and colorful flowers.

4.93 out of 5 average rating, 41 reviews

Beautiful 2 bedrm cottage in Beach Dreams complex

4.89 out of 5 average rating, 36 reviews

A comfortable outdoor space is presented with a grassy area surrounded by trees. Blue chairs are arranged around a fire pit, and large windows of the two-story home reflect the natural light. A sense of privacy is offered by the surrounding foliage.

Cottage in Casco

Waterfront Getaway w/ Private Beach (HOT TUB)

The exterior of the studio is shown, featuring a main entrance with large windows that provide natural light. A charcoal grill is positioned nearby, along with two blue adirondack chairs on a simple porch. The area is surrounded by gravel and concrete, with green grass visible in the background.

4.93 out of 5 average rating, 69 reviews

Cottage in Wells Maine

A spacious living area features large windows with natural light entering from outside, highlighting the blue walls. Comfortable seating includes a sectional and a leather ottoman. A decorative lamp and stylish clock add to the serene ambiance, while views of the surrounding greenery are visible.

4.98 out of 5 average rating, 66 reviews

2 BR house, close to Ogunquit, w/ AC + golf cart!

A bright kitchen area features modern white cabinetry and a spacious countertop. Barstools with woven seats are positioned at the counter. Natural light floods in through a nearby door, illuminating the polished wooden floor and light blue walls.

4.95 out of 5 average rating, 166 reviews

Cozy Cottage with Ocean Views, Wells Maine

Pet-friendly cottage rentals

4.99 out of 5 average rating, 141 reviews

A single-story cottage is nestled among trees, featuring a light yellow exterior with dark shutters. The well-kept front yard showcases a carpet of fallen leaves, and a small deck is visible to the right, enhancing access to the inviting outdoor space.

Cottage in Alton

“Stay Awhile in the Lake's Region”

4.98 out of 5 average rating, 84 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.

4.9 out of 5 average rating, 49 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

4.82 out of 5 average rating, 67 reviews

The kitchen area features wooden paneling and a practical layout. A dining table with four chairs is positioned beside a fully equipped kitchenette, which includes a stove, refrigerator, and essential appliances. Natural light fills the room through a window adorned with light curtains.

Cottage in Laconia

Charming and Cozy Cottage in Laconia

4.82 out of 5 average rating, 111 reviews

A bright, open kitchen and living area is designed with large windows allowing natural light. A central island with chairs offers space for dining or socializing. A comfortable seating area is visible, complemented by warm wood accents and serene artwork on the walls.

Cottage in Lyman

RK North : All season Waterfront cottage with dock

4.89 out of 5 average rating, 109 reviews

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.

Cottage in Gilmanton

Sawyer Lake Bear House

4.93 out of 5 average rating, 101 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

4.97 out of 5 average rating, 123 reviews

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.

Cottage in Gilmanton

Private Beach, Lake Front, Family Friendly Cottage

Private cottage rentals

5 out of 5 average rating, 84 reviews

The spacious living area features large windows allowing ample natural light, with modern furnishings including a comfortable gray sofa and decorative plants. A circular staircase leads to the loft space, while a cozy area rug adds warmth. A television is mounted on the wall for entertainment.

Cottage in Cornish

The Lil'house - A Mountain Top Modern Cottage

4.99 out of 5 average rating, 78 reviews

A cozy entryway features a welcoming porch with a hanging fern plant beside a large window. An adirondack chair is set against the wall, positioned near a wooden side table. A doormat greets guests at the entrance, contributing to the inviting feel of the space.

Cottage in Wolfeboro

King’s Cottage PERFECTLY LOCATED!

5 out of 5 average rating, 67 reviews

A deck view displays a serene lake surrounded by trees, with boats visible on the water. In the foreground, a wooden railing frames the scene, complemented by an umbrella and lounge seating. The cloudy sky adds a calm ambiance to the setting.

Cottage in Laconia

Charming Lake & Mountain escape. Fantastic views

4.92 out of 5 average rating, 86 reviews

The cottage features a welcoming exterior with red siding and large windows allowing natural light. Two wooden staircases provide access to the entrance, surrounded by greenery that complements the home’s peaceful setting.

Cottage in Acton

The Cozy Cottage at Loon Pond, Netflix

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

4.9 out of 5 average rating, 91 reviews

A charming log cabin is surrounded by greenery, featuring a red metal roof and large glass sliding doors. A wooden deck is adorned with vibrant seating options, creating an inviting outdoor space. Lush plants and trees frame the entrance to the cabin.

Cottage in Pleasantdale

Lakeside Story - Log Cabin, Fire Pit, Beach!

4.71 out of 5 average rating, 35 reviews

A charming cottage exterior is shown, featuring a light green facade and a pitched roof. The large deck showcases decorative American flags. Surrounding greenery adds to the natural setting, with a gravel pathway leading to the entrance. Inflatable pool toys are casually placed nearby.

Cottage in Tuftonboro

Cozy Lake Access Cottage With Deck.