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.

4.94 out of 5 average rating, 219 reviews

The exterior of the Carriage House is highlighted by rustic wooden siding and a welcoming entrance. A fire pit is surrounded by seating, creating a cozy outdoor gathering space. Lush greenery frames the area, contributing to a serene atmosphere.

Cottage in Tamworth

*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!

4.94 out of 5 average rating, 133 reviews

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

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

4.86 out of 5 average rating, 208 reviews

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

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.

4.99 out of 5 average rating, 167 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! 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, 130 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!

4.96 out of 5 average rating, 101 reviews

A cozy cottage exterior is depicted, featuring white siding and a green roof. A screened-in porch with comfortable seating is prominently displayed, along with a wooden entrance staircase. The surrounding area includes natural vegetation and a pathway made from red bricks, providing a welcoming access point.

Cottage in Standish

The Loon's Nest Cottage

Located only 30 minutes from Portland this adorable and cozy cottage sits 10 feet from Watchic Lake. Listen to the loons all day, paddle to an island, stare at the glassy lake from the breakfast nook, swim forever, read a book in the screened-in porch or toast marshmallows in the firepit, whichever it may be you'll simply enjoy the peace and tranquility of this very private Maine lake house nestled in the woods. If you’re feeling like a hike, a dinner out there are options a plenty!

4.97 out of 5 average rating, 169 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, 181 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, 226 reviews

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

☀ 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!

4.99 out of 5 average rating, 285 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.

4.98 out of 5 average rating, 112 reviews

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

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 cottage rentals in Ossipee

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A modern kitchen features white cabinetry paired with stainless steel appliances. A large island with four wooden stools provides ample space for dining or work. Natural light fills the area through a window, enhancing the clean, inviting design.

4.97 out of 5 average rating, 72 reviews

Freshly Renovated, Family-Friendly Coastal Cottage

4.82 out of 5 average rating, 78 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, 36 reviews

Cottage in Shapleigh

Cottage in the Pines | Lakeside + Pool + Hot Tub

4.88 out of 5 average rating, 126 reviews

The exterior of the camp is surrounded by trees, featuring a screened-in porch and large windows. A flag is displayed on the front, and gravel paths lead to the entrance. The building is designed to blend with the natural landscape.

Cottage in Gilmanton

Cozy cottage near Gilford, lake access & hot tub!

5 out of 5 average rating, 79 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

A grassy area features seating made up of Adirondack chairs and a patio table set, facing a row of cottages with large windows. The clear sky above is dotted with clouds, complementing the peaceful surroundings.

4.93 out of 5 average rating, 210 reviews

Wells Maine Home with a View

4.97 out of 5 average rating, 115 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

4.99 out of 5 average rating, 142 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”

4.85 out of 5 average rating, 13 reviews

A wooden dock extends into the vibrant fall-colored landscape, leading towards a charming house with large windows. A rowboat rests gently on the water's edge, while colorful kayaks are lined up beside it. Comfortable seating is arranged on the lawn, inviting relaxation.

Cottage in Shapleigh

Family & Pet Friendly, Lakefront Home

5 out of 5 average rating, 46 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

4.88 out of 5 average rating, 180 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

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

4.87 out of 5 average rating, 220 reviews

A cozy bedroom features a spacious bed adorned with a patterned blanket, flanked by two black nightstands. Nature-inspired wall art displays mountains and trees, complemented by plaid curtains. A vibrant area rug adds warmth to the wood flooring, creating a welcoming atmosphere.

Cottage in Gilford

A: Summer, Lake, Ski, Hike, Concerts

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

4.78 out of 5 average rating, 334 reviews

A charming cottage exterior is showcased, featuring a sloped roof and wooden steps leading to the entrance. Lush greenery and well-maintained shrubs surround the home, while a patio umbrella provides shade on the deck. A spacious yard with mature trees adds to the serene setting.

Cottage in Cape Neddick

Sweet cottage in quiet convenient coastal setting.

Private cottage rentals

4.93 out of 5 average rating, 44 reviews

A peaceful lakeside scene is presented, featuring a sandy area bordered by tall pine trees. Four black Adirondack chairs are arranged around a small table, with red and white striped blankets draped over them. The calm water reflects the surrounding green hills, creating a serene atmosphere.

Cottage in New Durham

Rustic Cabin w/ SUP boards, Kayaks, Canoe, Firepit

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

4.96 out of 5 average rating, 137 reviews

The entrance features a blue door with glass panels, surrounded by multiple windows. Lush hydrangea bushes in various colors are planted near the door. A welcome mat with an anchor motif lies on the gravel path leading to the entrance.

Cottage in Kennebunk

Cozy cottage

4.96 out of 5 average rating, 46 reviews

A tranquil lake scene at dusk, with the moon rising over the hills in the background. The water reflects the moonlight and nearby lights, creating a serene atmosphere. A small dock labeled 'LAKEHURST' is visible in the foreground, surrounded by soft white flowers.

Cottage in Alton

Lakehurst Lakefront Cottages #5

4.99 out of 5 average rating, 77 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, 72 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, 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