Vacation rentals in Ossipee

4.89 out of 5 average rating, 204 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, 114 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, 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.

4.85 out of 5 average rating, 350 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.

4.96 out of 5 average rating, 78 reviews

A covered porch area is furnished with two white wicker chairs, accompanied by decorative pumpkins and colorful autumn leaves. String lights are draped along the railing, creating a welcoming outdoor space that invites relaxation in a residential setting.

Apartment in Northfield

The Lady Grand at Northfield

Comfy, Private, First Floor Appartment. Self Check-In, Parking New England vacation rental within walking distance to our scenic historic main street. Centrally located to bike parks, white water park, numerous skiing and hiking options. In an hour's drive, it is possible to be at the shore, in the mountains or one of our great cities! Our guest suite has a private entrance to a mud room and is fully furnished, full kitchen and bath and can sleep up to 6 people.

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.

4.95 out of 5 average rating, 151 reviews

A colorful Welcome to Kennebunkport sign stands prominently at the bridge entrance. Below, a charming red building on stilts is seen, featuring a conical rooftop. Surrounding structures showcase classic New England architecture, enhancing the coastal charm of the area.

Home in Kennebunk

Quiet cozy cottage close to restaurants, beach

Winter-wonderland, close to skiing and a walk from great dining. In the summer, enjoy the quiet backyard or walk to the beach! No need to find parking, my place is 3/10 of a mile from downtown Kennebunkport and 7/10 of a mile to Gooch's Beach. You will love my place because of the kitchen, the coziness, and the location. My place is good for couples. It has a tempurpedic king-sized bed and a queen sized pull out bed in the living room.

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.

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What guests are saying

Charming Kennebunkport

4.93 out of 5 average rating, 29 reviews7 months ago

My husband and I stayed at Kristen’s apartment for 2 weeks at the end of August and had the most amazing time! This was our 3rd time to KPT and most definitely our favorite thanks to this gorgeous Airbnb and Kristen’s hospitality. The apartment was perfect for us — was exactly as described, better than the photos with amazing windows and views, speedy WiFi perfect for working remotely. It’s a quick 4 minute drive into town, and such a beautiful area to walk around. Kristen was so responsive and helpful — there’s a super extensive list of local reccs in the apartment, and a beach pass that you can use during your stay. We loved this home away from home, and can’t wait to come back soon!

Apartment in Kennebunkport

What guests are saying

Honey Bear house Close to all Storyland & village

4.91 out of 5 average rating, 70 reviews5 months ago

We were a group of 10+ women ranging in ages from 16 to 60 something. Moms, sisters, cousins, aunties and long time friends gathering for our annual “girls weekend”. A tradition spanning over 30 plus years, our group’s dynamics may have changed a bit - but not our excitement of coming together once a year. For the size of our group we require some standard needs: enough beds to sleep comfortably, enough bathrooms to accommodate all of us, a decent size cooking area, plenty of room for us to be social and room for all our vehicles. The Honey Bear House checked all those boxes. Kerri was very attentive to us, checking in on us at the start of the weekend and quickly responding to our texts. The house was as she describes it, plenty of dishes, silverware, cooking utensils, pots/pans, bowls & appliances, toaster & toaster oven, drip coffee & Keurig, lots of mugs! We supplemented with paper products & personal towels. Perfect spot for an extended family gathering!

Home in Intervale

What guests are saying

Hoyts Ahoy

5 out of 5 average rating, 25 reviews1 month ago

We had a wonderful weekend celebrating St. Patty’s Day up in Ogunquit. The property was everything we had hoped for in a rental. Everything was comfortable and clean. The house is spacious and a great place to get your day started. You can’t beat the location! Off the beaten path, but a few minutes of walking to downtown. The host was super responsive to my questions. I would absolutely stay here again.

Home in Ogunquit

What guests are saying

The Sommet-Magical Views- Main house+Guest cottage

4.98 out of 5 average rating, 54 reviews2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

Home in Jackson

What guests are saying

SeaRose Cottage, Sleeps 10, Cape Neddick ME

5 out of 5 average rating, 9 reviews7 months ago

Would definitely stay again. Stephen was a great host and was responsive to all our needs, even including a thoughtful welcoming package. The house was absolutely spotless and very comfortable. Plenty of hot water for showers for our big group. Just FYI if you plan on cooking, bring your own spices. The house is a walk away to Perkins Cove but was still an oasis in the woods for tranquil sleep.

Home in York

What guests are saying

LUX Home with Breathtaking Views

5 out of 5 average rating, 6 reviews4 days ago

We had such a wonderful stay at this beautiful luxury home! It was a moms’ getaway with our kids (ages 8 to 12), and it was exactly what we needed. The home itself is stunning—spacious, clean, and full of charm, with incredible views from almost every window. I loved waking up early, sipping coffee with a book outside or by the big windows, just soaking in the peaceful surroundings and a fresh air. There was so much for the kids to do, and we had some busy, fun-filled days—lots of hiking, stops at McDonald’s, and some really cute local restaurants and breweries all within 15 minutes. It felt like the perfect mix of adventure and relaxation. Tim is amazing—so proactive, always quick to respond, even when I was delayed in getting back due to our packed schedule. He was kind enough to offer a complimentary late check-out since the cleaning crew was scheduled for later, which was a win-win and much appreciated. We would absolutely love to make this an annual trip. highly recommended!

Home in Franconia

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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

4.92 out of 5 average rating, 38 reviews

An airy living space features a modern spiral staircase leading to an upper level. Large windows allow natural light to fill the room, highlighting the wood flooring. A cozy seating area with a sofa and armchair can be seen in the background, contributing to the open design.

Home in Ogunquit

Ogunquit Beach House - New Listing -Great Location

4.87 out of 5 average rating, 117 reviews

An indoor spa area features a large hot tub with bubbling water, surrounded by tiled flooring and wooden walls. A mural of palm trees against a beach backdrop adds a tropical feel to the space, enhancing the relaxation atmosphere.

Home in Lincoln

Luxury Home with Outstanding Views!