Holiday rentals in Ossipee

Derby House

Relax with the whole family at this peaceful quintessential lake house. Located on the shore of Lake Winnipesaukee in Chestnut Cove. The Derby house has 100 feet of private waterfront, beach and a large deep water crib dock. Relax and dine on the large deck by day and sit by the waters edge and enjoy a crackling fire while star gazing at night. There is plenty of space for your boat, kayak, canue etc. Kids and adults alike will enjoy the sandy beach with easy access to swimming & snorkeling.

Cozy Cabin Retreat just off Lake Ossipee

Nestled on 17 acres and backed by 400 acres of Ossipee Forest just off Lake Ossipee, this cabin is perfect for a quiet retreat or a home base for all the splendor NH has to offer. Sit by the fire with your favorite book and beverage or cook your favorite meal in the full kitchen. The wrap around screened in porch is a great place to enjoy company or stare off into the woods looking for wildlife to wander by. No matter the season this cabin is close to all your favorite outdoor activities.

Beautiful Two Bedroom Overlooking Long Lake #2

Gorgeous renovated two bedroom overlooking Long Lake. Fantastic views from each room! Watch the morning sunrise from your bed or take in the view from the peninsula with private sandy shallow entry beach. Open concept modern kitchen and living room make a great space for couples, friends or families. Go explore by kayak, read under a tree and smores by the firepit! Enjoy the huge lawn with a game of volleyball or soccer. Use of boat slip upon request and availability. Connects to Sebago!

Baby Chocorua A Frame in the mountains sleeps 8

*2 Nite minimum rental only no max* pet friendly Baby Chocorua,, 3 bedrooms, one king, 2 queen, 2 twin beds. 2 bathrooms. high-chair and pack and play for toddlers. spacious Living room & kitchen area with electric fireplace & reclining sofas. Dining room table seats 8 converts to a pool/ping pong table for after dinner fun. video game room Complementary EV charging station, driveway accommodates up to class A RV, free use 8 Kayaks with life jackets if you can transport?

*Renovated July 2023* Kimball Getaway

Lakefront cabin with small kitchen, living space, and bedroom that sleeps two. Bathroom has toilet and sink and there is an outdoor shower around back. There are two separate decks, one with stairs to the water and second private deck for the bedroom. Cabin comes with a fire pit, picnic table, grill and black stone skillet. Motor boats are allowed on the lake with the boat launch 0.5 miles away. Located in a great community, very quiet and private compared to larger lakes.

Peaceful Ossipee Lake Cottage Private Beach/Dock

Enjoy making memories at our cottage steps from Leavitt Bay on Ossipee Lake, one of the prettiest lakes New Hampshire has to offer. Swim, kayak, and fish right from the property's dock on your own private beach. You can use our kayaks or bring your own boat! Listen to the loons, watch the eagles soar, and roast marshmallows by the fire. Find all of this and more at this cozy lakefront cottage featuring 2 BR, 1 BA with beautiful panoramic lake & mountain views.

Lake Front Cabin with Private Dock & Amazing Views

Escape from the hustle and bustle of everyday life at this charming lakefront home on beautiful Merrymeeting Lake. With your own private lake access, dock, multi level decks, & waterfront yard, you can spend your days swimming, boating, or simply relaxing by the water. Enjoy a spacious outdoor area perfect for relaxing, dining, or stargazing. Sleeping up to 8, it's ideal for a peaceful getaway with all the comforts of home for couples, families, & small groups!

The Country Cottage in Sanbornville

Your family will be close to a majority of popular NH attractions while staying at the cottage. The cottage is totally separate and brand new as of 2023, attached to our old farmhouse circa 1789 in the beautiful lakes region. It’s a perfect place for couples, small families or traveling nurses/doctors. We are 10 minutes from several beaches including lake winnipsaukee and close to the mountains. There are several hiking trails within minutes from our home.

HOTUB! Riverfront, dog friendly, close to skiing!

The Hot Tub is warm and inviting this time of year! Relax and enjoy this Riverfront Retreat! Ski @ King Pine(15 min.), Cranmore & Attitash (30min.), shop, ski & dine in North Conway. Nearby restaurants- Hobbs, Jakes Seafood, Yankee Smokehouse,Pizza Barn! Plan your Amazing get-away now! Perfect for a couples escape, family fun, girls weekend or a guys getaway! *6 guest max. *2 outdoor motion sensor security cameras on site. * 4wd is a must for snow season

Kirkland Cottage (A ski and lake escape)

Welcome to Kirkland Cottage! Located a two minute drive from Ossipee Lake and near the White Mountains, we are a great base for all New Hampshire has to offer! Explore lakes, mountains, and hiking trails, while being just an hour from Portland and Portsmouth. Kirkland Cottage house is 9 minutes to King Pine Ski area, 30 minutes to Cranmore, and 25 minutes to North Conway, which has great shopping, skiing, hiking, and lots of restaurants.

Ossipee Lake Waterfront Condo

Large, open, and bright. My condo on Lake Ossipee has four levels of relaxing living space, including beds to sleep 6 (max allowed per new Ossipee permit rules). One king, one Queen and two pairs of Twins in four bedrooms. Open plan, comfortable living room and den along with granite in the kitchen, new hardwood floors and tile throughout. 3.5 baths including a master bath, make this house very comfortable for large families and groups

The NEST Haven awaits you.

You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.