Cottage holiday rentals in Ossipee

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.

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.

*5-Star CLEAN *Outdoor Shower *Private Yard *Grill

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!

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.

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.

Unique Waterside Cottage - White Mountains, NH

Idyllic, serene waterside cottage. The private deck perched over the 32 acres of spring-fed, trout stocked-water is perfect for romantic sunsets. Enjoy the turtles as your feet dangle over the deck. The detailed cottage has wi-fi and comes with a well-equipped kitchen, and quality bedding, and is ideal for 2 people. Relax, read, fish, listen to the loons - a perfect get-away to completely unplug. Great hiking, kayaking, and biking in the area. Grill, hammock, and fire-ring by water's edge.

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!

Conway Waterfront Base for Your Family Memories!

Waterfront gem in the middle of it all! Designed to be the ideal getaway regardless of the season. Beautiful views out master bedroom, the back porch and from the backyard year round. The feel of seclusion while still being near all activities! Enjoy the water on one of the two kayaks or in the 2 canoes. Perfect base for skiing, hikes and sightseeing! Easy drive to North Conway, Kankamangus Highway, White Mountains, Story Land and so much more! No need to leave the property, just enjoy!

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.

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.

The Lake house

Enjoy the southern exposure, a sugar sand walkout beach, an L-shaped dock, and classic Lake Winnipesaukee construction. The open concept includes a full kitchen and a living room. The spacious bathroom also includes a washer and dryer. It has one private bedroom, and a ships ladder guides you to a loft containing additional sleeping space, with a catwalk to a private balcony overlooking the lake. This property has a detached bunkhouse with two full-sized beds and a ¾ bath.

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.