
Holiday rentals in Sullivan
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Top-rated holiday rentals in Sullivan
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Cozy Comfort on 250 Acre Private Estate
If you’re looking for serenity, peace and quiet, you've found it, amidst a 250 acre private estate. On a lake at the end of a mile long driveway (well plowed in the winter) Is Snowshoe Cabin. Built in 1929 as the garage for "Lakefalls Lodge, it's been completed renovated into a luxurious, cozy home with modern amenities. Guests rave about "views of the snowy pond while you’re warm inside" from heated floors and a wood burning stove with free firewood. Spikes provided for wonderful winter walks.
4.98 out of 5 average rating, 254 reviews
Peaceful lake/mountain house & close to skiing
If you are looking for peace, comfort, and relaxation this year it can be found at Grateful Ledge. This new custom lake/mountain house is a perfect escape from reality. With the lake, hiking trails, ski mountains, and other wonderful attractions in the area, you can find numerous ways to unwind in nature. Grateful Ledge is two hours from Boston, and an easy drive from CT/NYC and the best spot for couples, families, or friend getaways. Enjoy Long Pond and appreciate all that you’re grateful for.
5.0 out of 5 average rating, 39 reviews
Cozy and Romantic Granite Lake Cottage Getaway
Welcome to "Corgi Cottage" ~ your private peaceful getaway to pristine Granite Lake. Enjoy sunrise over the lake from the deck and sunset over the backyard barn. In between, spend the day on the lake in your private sandy cove with dock, fishing, hiking or relaxing. Three mile lake road for walking or biking. The area offers many hiking trails and Mt. Monadnock only 30 minutes away. Small convenience store offers basic amenities while Keene’s many shops and restaurants are only 15 minutes away.
4.99 out of 5 average rating, 144 reviews
Sunapee area lakeside cottages trio on Sand Pond
Three cottages, each with lake view and shared dock, on pristine, quiet Sand Pond are perfect for a family gathering. Three cottages for one rental, offering privacy and indoor and outdoor space for being together. The main cottage sleeps four, has a full kitchen and a screened-in porch; the two studio cottages have kitchenettes and sleep two. It is not ideal for very young children or those who have difficulty walking up and down hill on uneven ground. 8.5% NH Meals & Rental tax applies.
4.88 out of 5 average rating, 112 reviews
Cozy Downtown Getaway!
Welcome to our charming Airbnb nestled near downtown Keene, New Hampshire! Our property offers a cozy and welcoming retreat for guests looking to experience the vibrant culture of this historic city. With its convenient location, you'll find yourself just a short stroll away from the bustling shops, eateries, and attractions that downtown Keene has to offer. The spacious Airbnb boasts 3 bedrooms, 2 bathrooms and ample living spaces making it ideal for families or groups of friends traveling.
4.86 out of 5 average rating, 81 reviews
Modern Lakefront Home
Relax with the whole family at this peaceful lakefront home. Enjoy breakfast overlooking the lake or read a book while listening to the soothing sound of water flowing over the dam. Located at the Southern end of Highland Lake there is little boat traffic. Enjoy the water for swimming, paddle-boating, kayaking or fishing. Leaf peeping in the fall or skiing, snowmobiling or ice fishing in the winter. Great location for large families or multiple families to get together and enjoy the day.
5.0 out of 5 average rating, 19 reviews
The Boat House on Granite Lake
Welcome to "The Boat House" ~ your private getaway on pristine Granite Lake. Enjoy sunrises over the lake from the deck with your morning coffee. Spend the day on the lake kayaking, fishing or relaxing on your private dock. Three mile road around the lake for walking or biking. The area offers many hiking trails. Keene’s many shops and restaurants are only 10 minutes away. Ideal for small families, couples, or a girls night getaway! This house is right on the water with amazing views!
5.0 out of 5 average rating, 29 reviews
The Brick House on Washington Street
Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.
4.93 out of 5 average rating, 249 reviews
The Harrisville Ranch - Monadnock Region Getaway!
Located in the heart of the Monadnock Region and surrounded by forests and lakes the Harrisville Ranch is ready to host you! With 4 bedrooms it is great for groups & families visiting the area for hiking, weddings, or just a getaway to a quaint NH village. Mount Monadnock: 5-15 minutes depending on the hiking trail Dublin School: 5 minutes Aldworth Manor & Mayfield Farm Venues: 8 minutes Harrisville Center: 5 minutes Peterborough: 15 minutes Hancock: 15 minutes Keene: 20 minutes
4.95 out of 5 average rating, 114 reviews
Swiss Chalet Family Retreat!
Welcome to our family's Swiss style chalet! Inspired by trips to Davos, Switzerland, my grandparents built the chalet in the 1950s to be a family playhouse and gathering spot for their 6 children. It's kind of magical. Today, our large extended family still enjoys holiday celebrations here every year. Our kids love exploring the woodland trails and swimming in Center Pond. We hope you love it as much as we do! Note: the building also has two apartments on the first floor.
4.88 out of 5 average rating, 112 reviews
Family-Friendly 3BR Historic Home – Walk to Keene
Stylishly renovated 1920s family friendly 3BR, 3BA home in the heart of Keene! Walk to downtown shops, restaurants, trails, and the Ashuelot River. Spofford Lake (16 min) offers swimming & kayaking, & Mt Sunapee (under 1 hr) is great for skiing & snow boarding. Enjoy an easy check in with smart lock, digital welcome guide, chef’s kitchen, fast WiFi, central AC, fireplace, smart TVs & fenced yard with patio and firepit. Perfect for families, friends, or remote work stays!
5.0 out of 5 average rating, 20 reviews
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Discover the ultimate outdoor experience in Southern NH! Enjoy a year-round private hot tub in a covered gazebo, fire pit, hammock, life-size games, and swing set. Located in one of Keene’s safest, quietest neighborhoods, walking distance to downtown and across from Keene Ice Rink. Close to beaches, hiking, and ski resorts. Features a fully stocked chef’s kitchen, wine cooler, and luxury Purple mattresses with individual mini-splits in each bedroom for optimal comfort.
4.98 out of 5 average rating, 209 reviewsPopular amenities for Sullivan holiday rentals
Other great holiday rentals in Sullivan

Lakeside Couple's Getaway
5.0 out of 5 average rating, 23 reviews
Heron Cove Cottage: A Sweetwater Stay
4.78 out of 5 average rating, 96 reviews
4 BR Monadnock View Luxury Chalet
5.0 out of 5 average rating, 24 reviews
Charming, Large House in Walpole NH /VT. Border
4.98 out of 5 average rating, 91 reviews
The Murdock Suite @ The Large House
4.95 out of 5 average rating, 80 reviews
Water view, 2 min to public beach, king beds
4.95 out of 5 average rating, 43 reviews
Lakeside Retreat 4BR/2BA- 2hrs from Boston
4.97 out of 5 average rating, 32 reviews
Rustic Charm in Stoddard – Lakeside Escape
4.93 out of 5 average rating, 15 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Berkshire East Mountain Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Snhu Arena
- Dartmouth College
- Ragged Mountain Resort
- Bear Brook State Park
- Hildene, The Lincoln Family Home
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- University of Massachusetts Amherst
- Montshire Museum of Science
- Mount Sunapee Resort
- Camp Plymouth State Park
- The Montague Bookmill
- Quechee Gorge
- New Hampshire Motor Speedway
- Jamaica State Park
- Bridge of Flowers





