Holiday rentals in Square Pond

Serene Lakefront Retreat in Southern Maine

Escape to our charming lakefront cottage, a serene haven by tranquil waters designed for couples and families seeking a peaceful retreat. Whether you're seeking a romantic getaway or a family vacation, our cottage offers the perfect setting for relaxation and adventure. Key Features: Stunning lake views, private dock and kayaks, and a spacious deck with seating, BBQ grill, and heater. Why You'll Love It: Peace and privacy, nature at your doorstep, perfect for all seasons, <2 hrs from Boston.

Luxury Year-round Hobbit House w/ private hot tub

Fern Hollow 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.

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.

Modern Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

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

Galinhas Getaway - Moosam Lake

This lake house is an incredible place to stay year round. The views of the lake are just breathtaking. The yard is a great size for small gatherings. Perfect for playing games and enjoying the fresh lake air. House is equipped with an outdoor grill & griddle, a fire pit for burning wood, and a gas fire pit on the lower patio. It has its own dock. Perfect for boating, kayaking, fishing & ice fishing. Local trails for ATV’s & snowmobiles. Skiing & snowtubing less than 45 mins away at King Pine.

Historic Schoolhouse c1866 + Pool + Lake + Hot tub

Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

The Lake House in Acton

Luxury at The Lake House in Acton – your Great East Lake escape! Enjoy this luxurious home as you sip your morning coffee on the deck, take a dip in the lake, warm up in the hot tub or explore the beautiful trails nearby. Enjoy the peaceful serenity of the lake with the lovely sounds of the loons in the background as you enjoy a drink by the fire or a good book on the couch near one of our two indoor fireplaces! Book your getaway at The Lake House – your new favorite spot in Acton!

Lakefront Retreat w/ Sandy Beach, 2 Docks + A/C

Our cherished family retreat in a serene cove on Mousam Lake offers 280’ of waterfront beach making it ideal for year round memories. Home boasts 2 kitchens making this ideal for large families. Home features A/C for summer and heated floors for winter. Enjoy two docks—perfect for boating—or take out the kayaks and paddleboard. For outdoor lovers, ATV and snowmobile trails are steps away. Winter brings nearby skiing at King Pine and North Conway, just 45 minutes away

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.

Camp on Goose Pond!

Escape to this peaceful camp with 50 feet of private shoreline on Goose Pond. Perfect for a relaxing getaway, this cozy retreat offers direct access to the water for fishing, swimming, and boating. Venture into nearby Mousam Lake by kayak or canoe for even more adventure. Whether you're unwinding on the deck, enjoying a campfire, or soaking in the lake views, this is the perfect place to unplug and make memories.