Vacation rentals in Isles of Shoals

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Family · Location · Layout

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Location · Family · Access

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Value · Location · Outdoor spaces

Salty Mermaid Cottage/Boat House

This 2br home is nestled at the end of a peninsula’s over the water, 5min drive to downtown Portsmouth. Spend the day on the on deck, grilling or enjoy your own authentic Maine lobster bake, swimming and treasure hunting the shore. Also explore Kittery or downtown Portsmouth, both just five minutes away. Enjoy this freshly renovated home, water views from every room and window, all bedrooms are equipped with a/c, free WiFi and smart TVs. Fully equipped kitchen has an amazing view of the water.

Value · Location · Hospitality

Moss House: A Modern Waterfront Cabin in the Woods

Featured in VOGUE and Maine Home + Design, this modern, handcrafted cabin offers calm Atlantic views, 150 feet of shoreline, and a private dock, perfect for morning coffee, launching a kayak, or watching seals, seabirds, and passing boats. Set among tall pines, it blends Nordic and Japanese influences in a space that is calm and composed. Interiors of wood, stone, lime plaster, and concrete form a grounded, quietly expressive, and sustainably built retreat. 1hr from Portland, but a world apart.

Family · Location · Access

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Value · Family · Outdoor spaces

*Beachfront* Vintage Coastal Cottage - Relaxation

It's always about the view and this place will leave you feeling energized and calm. Situated on premium beachfront property, this single family home has luxurious amenities like super plush towels, organic cotton bedding and touches to make your getaway feel that much Take a virtual tour here once you book I can send you a link (per Airbnb’s rules) I’ve outfitted it with an extra monitor & a setup o WFH. Google home and Sonos systems bring this 100 year old beauty into this century.

Value · Family · Long stay

The Copper Fox Treehouse

Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse

Value · Family · Outdoor spaces

The Maine Frame | Modern A-Frame Cabin in Freeport

• Perfect for small families or couples, our signature A-Frame cabin features a modern interior gas burning fireplace, soaring ceilings, huge windows, stylish interiors, and all the comforts of home. • This cozy 1,100 square foot space comfortably accommodates up to four guests in two bedrooms (one with a King-size bed and the other with a Queen-size bed) and a shared bathroom. • 7 minute drive to downtown Freeport. • Proud to be ranked in the top 1% and voted Guest Favorite!

Family · Location · Cleanliness

A water view slice of heaven at Pepperrell Cove

Enjoy the peace and tranquility of staying in Kittery Point Maine’s exclusive Pepperrell Cove area. • Walk three minutes to dinner at one of three amazing waterfront restaurants • Enjoy a private chartered boat ride from across the street • Rent kayaks • Visit Fort McClary • Hike Cutts Island Trail • Visit Crescent and Seapoint beaches • Shop and dine in Kittery’s Wallingford Square, downtown Portsmouth, and the Kittery Outlets. Everything is within fifteen minutes away!

Family · Location · Layout

Chic Loft-Style Condo in Downtown Portsmouth

This contemporary loft-style condo in Portsmouth , is located directly on the Piscataqua River, offers two bedrooms, a comfortable living room, vibrant dining space, and galley kitchen. It's a short walk to all of the shops and restaurants in downtown Portsmouth, and just 8 miles to New Hampshire's most popular beaches. Come relax, dine, shop and play. It's all here for your enjoyment, and you just know it's time to book yourself getaway!

Value · Family · Sleep quality

Romantic Mirror cabin in the woods

Stay at Hidden Pines Cabins. The Mirror cabin is Maines only 3 sided floor to ceiling mirrored glass cabin. Unwind in the hot tub while looking up at the sky full of stars. Take a sauna while surrounded by nature all around. Located in the majestic forest of mount Agamenticus, the extensive trail system is off of our road. Short drive to the Ogunquit/York beaches, Outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

Location · Value · Access