Vacation rentals in Ossipee

4.89 out of 5 average rating, 205 reviews

Condo in Kennebunk

Over 1000 Five Star Reviews! Walk to Dock Square !

Free onsite parking for 1 car. Beautiful coastal décor and modern amenities makes this a perfect choice for your vacation. Walking distance to EVERYTHING! Dock Square is a 1 minutes walk. Music, Art and Fine Dining surrounds you. Lots of windows and a slider to the deck make this location bright and airy 2 private decks for your enjoyment, two bedrooms, 2 full bathrooms. Perfect for couples or families. Parking for one car in lot, added public park across s NO PARTIES Pets considered

4.83 out of 5 average rating, 115 reviews

A welcoming cabin is situated down a gravel driveway surrounded by tall trees. Warm light spills from the windows, creating a cozy ambiance as dusk settles. A lantern beside the pathway adds a gentle glow, inviting guests toward the entrance.

Home in Conway

A Large Vacation Home with hot tub, game room +

My place is close to family-friendly activities, skiing, snowboarding, golf, shopping, hiking, restaurants, night life, shoe shoeing, ice skating, sleigh rides, tubing, Saco River tubing/canoeing, Echo Lake, Gondloa rides to summit, mini golf much more. You’ll love my place because of the quiet neighborhood, comfy beds, the kitchen, the hot tub and fireplaces and the space for large reunions and gatherings . My place is good for couples, business travelers, families (with kids), and big groups.

4.98 out of 5 average rating, 330 reviews

A wooden dock extends over vibrant green marshland, leading to a serene body of water. Lush trees and rolling grass create a peaceful backdrop, emphasizing the natural beauty of the surroundings.

Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

Tastefully appointed 1 bedroom apartment one mile from desirable Dock Square, Kennebunkport. This apartment features Panoramic views of the famous Cape Arundel Golf Course and Goff's Brook Tidal River. Private, secluded back deck with dining and lounge areas, Cozy furnishings throughout, King sized bed with memory foam topper, Fully Equipped Kitchen, and more! At Cape Arundel Cottage, guest experience is our highest priority! *See “other things to note” for additional important information.*

4.94 out of 5 average rating, 128 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

4.94 out of 5 average rating, 161 reviews

The exterior of a spacious mountain townhome is captured, featuring a warm wood façade and large windows that allow natural light inside. A deck extends from the front, overlooking a snowy landscape, with tall trees framing the serene setting.

Home in Carroll

Cozy Townhouse: Bretton Woods Mt. Washington Place

In the Mount Washington Resort (Bretton Woods) and near Cannon Mountain. Inviting four-season end-unit town home with warm ambiance, all the comforts you need, and great views. A mountain vacation getaway at a great value. Modern kitchen, comfortable dining and living room with fireplace. Four bedrooms, three floors, each with private bathroom (three full, one with shower). Large entertainment / recreation room for the family, outside deck with seating to enjoy the wildlife and a grill.

4.96 out of 5 average rating, 160 reviews

A stone fireplace with a modern design is centered against a rustic wall, featuring stacked firewood on either side. The warm glow of the fire illuminates the surrounding area, complemented by natural wood beams on the ceiling.

Condo in Lincoln

Gorgeous River & Loon Mountain View Studio Condo

Cozy Studio Condo in hotel resort community sleeps 3. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy Lovely views of the mountain and Pemi River! You'll love the nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

4.84 out of 5 average rating, 352 reviews

A natural rock formation features small waterfalls cascading into a clear pool. Surrounding greenery adds a touch of nature, while guests are seen enjoying the water. Sunlight reflects off the rocks, creating a warm atmosphere.

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

PLEASE DO NOT BOOK PEAK HOLIDAYS/WEEKENDS IN ADVANCE as we try to rent the entire house 1st. We book this listing as a 1 bedroom ONLY. Directly in the village! yet tucked away, private YARD, HOT TUB, fireplace, new furniture, cozy beds and & linens. WALK to restaurants, Saco River, Golf, Village Green, Rec Center, Whitaker Woods, scenic train station, coffee shops, stores, skating, Cranmore & nightlife. Enjoy Kayaking, skiing, adventure parks, skiing, story land, hiking, etc.

Townhouse in Kennebunkport

A sandy beach scene is captured, featuring colorful kayaks arranged neatly in the foreground. Sunbathers and beachgoers enjoy the sunny weather, with umbrellas dotting the shoreline. A smooth ocean extends to the horizon, framed by a clear blue sky.

4.94 out of 5 average rating, 167 reviews

Great get away spot,historic home in Kennebunkport

Located 1.8 mi-dock square, 2.6 mi- Colony Beach, .7 mi -Cape Arundel Golf Course. Plenty of onsite parking, beach pass provided for Kbunk Beaches, a large back yard for fun and relaxation. Just on the outside of town in a country setting. Comfortable setting for relaxation. This is a daily reservation from Oct.1st-June. I love to make sure my guests have as much fun as they can while they are visiting and will help out in anyway possible. No dogs of any kind are allowed

4.85 out of 5 average rating, 105 reviews

A spacious living area features a large sectional sofa, a coffee table, and a flat-screen television. Natural light pours in through large windows, complemented by a skylight. A cozy fireplace is situated beside a textured black rug on the floor, adding warmth to the space.

Townhouse in Bartlett

Spacious Family Vaca Storyland*Saco*Close to all!

Your family will be close to everything when you stay at this spacious, centrally-located place. Pool access to renters. Popular Game room just added! Less than 10 minutes to Storyland and North Conway Center, and 40 minutes to Santa’s Village. Great access to Cranmore and Attitash for Skiing, town of Jackson, and numerous hiking trails. Access to Saco River just steps away! Wonderful space for the whole family, multiple areas to spread out. Brand new fire place.

4.93 out of 5 average rating, 352 reviews

A serene river flows through rugged granite formations, surrounded by vibrant autumn foliage. Tall trees flank the banks, showcasing a mix of greens, yellows, and oranges. The distant mountains rise gently under a clear sky, creating a tranquil natural landscape.

Condo in Lincoln

Cute Studio Apt Resort Lincoln, NH Loon Mountain

Quaint Studio Apartment, Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Skiers & snowboarders enjoy the Free Shuttle to Loon Mountain Ski Resort only minutes away. Great area dining, and outdoor activities, indoor pool, outdoor pool, Sauna, Jacuzzi and game room make this is a great vacation location for your family. Great restaurants within walking distance.

4.88 out of 5 average rating, 317 reviews

A cozy loft bedroom features a wooden ceiling with exposed beams. A spacious bed is positioned centrally, flanked by two bedside lamps on dark nightstands. Light filters through a window adorned with curtain panels, illuminating the rustic wooden walls and framed artwork.

Cabin in Woodsville

Cabin Getaway, Pool Tb, Darts, Poker Tb, ATV Trail

Log cabin getaway in White Mountains, NH. Located in Mountain Lakes community, it is a perfect location from which to enjoy outdoors. You can fish, swim, hike, ski and then come back to a comfortable home. Sit on the deck and pick at the mountains or enjoy a get together by the big fire in the yard. Easy walk to the lakes. Close to trails for ATV and snowmobiles. Visit nearby towns of Lincoln, Littleton, Franconia with lots of restaurants and activities.

4.92 out of 5 average rating, 167 reviews

Condo in Lincoln

Cute Resort Studio Apt with Pool, hot tub at Loon

Relax with the whole family at this peaceful place to stay. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Ossipee vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Ossipee's top sights

Hobbs Tavern & Brewing Company68 locals recommend

White Lake State Park34 locals recommend

Yankee Smokehouse26 locals recommend

Pizza Barn20 locals recommend

Rosie's Restaurant19 locals recommend

Jake's Seafood and Grill18 locals recommend

Other great vacation rentals in Ossipee

4.99 out of 5 average rating, 68 reviews

An inviting exterior view of the property showcases a red house surrounded by lush greenery. String lights illuminate the outdoor seating area, which includes comfortable chairs and a hot tub, creating a serene atmosphere for relaxation.

Home in Thornton

70 Acre White Mountain Estate – Panoramic Views

4.92 out of 5 average rating, 13 reviews

A wooden dock extends into a calm lake, surrounded by lush green mountains. A boat is tied next to the dock, while a lounge chair sits invitingly on the platform. The water reflects the serene landscape, creating a peaceful atmosphere.

Cabin in Greenwood

All seasons Lake House next to ski areas

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

5 out of 5 average rating, 49 reviews

A spacious two-story house overlooks a lush green lawn, featuring multiple seating areas with wood chairs arranged around a fire pit. Large sliding doors open to balconies on both levels, providing views of the surrounding landscape and lake.

Vacation home in Tilton

Cheerful 4 bedroom, lake-front vacation home

4.92 out of 5 average rating, 179 reviews

A charming log cabin with a gabled roof is set against a clear blue sky. Large windows enhance the natural light and provide views of the surrounding trees. A spacious deck features outdoor seating, surrounded by stone steps leading to the lush green yard.

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping

4.96 out of 5 average rating, 45 reviews

A spacious deck is highlighted, featuring a circular table and two chairs, with a scenic view of surrounding greenery and distant mountains. Sunlight bathes the area, creating a bright and inviting outdoor space for relaxation.

Home in Haverhill

White Mountains Cottage w/ Mountain & Lake Views!

4.92 out of 5 average rating, 38 reviews

The living area features a modern design with high ceilings and large windows allowing natural light to fill the space. Two comfortable sofas and two armchairs are arranged around a round ottoman. A small side table and a television provide additional amenities.

Home in Ogunquit

Ogunquit Beach House - New Listing -Great Location