BOOK between 9/10 and 9/30/25 - Fall Escape: Two nights or more in October includes a complimentary bottle of wine or champagne as a welcome gift.         BOOK between 9/10 and 9/30/25 - Fall Escape: Two nights or more in October includes a complimentary bottle of wine or champagne as a welcome gift.         BOOK between 9/10 and 9/30/25 - Fall Escape: Two nights or more in October includes a complimentary bottle of wine or champagne as a welcome gift.        

A Cozy Winter Retreat: Romance in Boothbay Harbor, Maine

Published: October 1, 2025

There’s something magical about celebrating love in a quintessential New England coastal town during the winter months. Boothbay Harbor, Maine offers an intimate getaway where couples can embrace the season’s charm while staying warm and cozy together. When the temperatures start to drop, there are more opportunities for snuggling and holding hands and nuzzling noses.

The Perfect Harbor Views

Boothbay Harbor transforms into a serene paradise during the cooler months. The summer crowds have long departed, leaving behind a peaceful waterfront where fishing boats gently bob in the harbor and seabirds glide over the calm waters. The occasional dusting of snow adds an enchanting layer to the historic buildings and weathered docks, creating picture-perfect moments for couples to capture. Bundle up in your cutest winter hats for an adorable selfie by the water.

Finding Romance at The Cottage at Five Gables Inn

While Boothbay Harbor offers several charming accommodations, The Cottage at Five Gables Inn stands out as an ideal retreat for a lovers’ getaway. This private cottage provides an intimate escape with thoughtful amenities designed for couples seeking both romance and relaxation.

The cottage’s crown jewel is its private hot tub, perfectly positioned to offer sweeping views of the harbor. There’s nothing quite like soaking in the warm, bubbling water while watching the sun set over the water, painting the sky in passionate pinks and deep purples. In the evening, the twinkling lights from boats and distant homes create a magical atmosphere as steam rises from the hot tub into the crisp air.

Inside, the cottage’s fireplace becomes the heart of your stay. After a day of exploring, couples can curl up together on plush seating, sharing a bottle of wine or cups of hot chocolate while the flames dance and crack in the hearth. The fireplace not only provides warmth but creates an inherently romantic atmosphere that encourages intimate conversations and quiet moments together.

The views extend throughout the cottage into the kitchen, dining area, and three bedrooms. Imagine waking up in the master bedroom as sunlight fills the room. As you sit up, across the room there are windows and glass doors to the balcony that look out over the water. If one of you sneaks out to make coffee you can start your day off slowly with coffee and water views in bed.

Romantic Activities in Boothbay Harbor

While it might be tempting to spend your entire stay in the cottage’s cozy confines, Boothbay Harbor offers plenty of romantic winter activities. Bundle up for a hand-in-hand stroll along the short walking path in Ocean Point. The Point offers majestic views of islands and lighthouses and can be quite busy in the summer months. The changing seasons means fewer people and chances spot to winter bird visitors such as scoters, grebes, and rare King Eiders.

For indoor entertainment, the Opera House at Boothbay Harbor often features special performances, from classical music to intimate acoustic shows. The historic venue’s architecture alone is worth admiring, with its restored Victorian details creating an elegant backdrop for an evening out.

The Boothbay Region Land Trust is open year-round and it has lots of fun winter activities and events:

  • Romantic sunrises and sunsets near Boothbay. The shore at Oak Point Farm faces south so you can catch the beginning or the end of the day together.
  • Go exploring together. Put on a sturdy pair of hiking boots and go looking for unique ice formations near the trail waterways.
  • Be kids again. The hill at Oak Point Farm is a favorite for sledding near Boothbay. BRLT has sleds to borrow or you can bring your own.

Culinary Delights for Two

Despite being a smaller coastal town, Boothbay Harbor’s culinary scene shines during winter. Many restaurants offer special menus featuring fresh-caught Maine seafood and locally sourced ingredients. There are many options for romantic dining at a restaurant in Boothbay during the off-season.

They say that oysters are known for having aphrodisiac properties, Mine Oyster has you covered with a menu featuring the freshest oysters. The Boathouse Bistro keeps the first floor dining room open for intimate winter dining; share a meal of tapas while chatting with the locals.

For a more casual but equally romantic experience, stop by Red Cup Coffee House in the morning. Share a warm breakfast and locally roasted coffee while watching the harbor come to life. Their house-made pastries and hearty breakfast sandwiches provide the perfect fuel for a day of exploration.

Shopping for Treasures Together

The quieter seasons allow couples to leisurely explore Boothbay Harbor’s unique shops without fighting crowds. Discover local artisan crafts at Abacus Gallery. The East Boothbay General Store is exactly as it sounds; pick up some boutique groceries to cook a meal at your cottage, grab a warm sandwich, or browse the eclectic gifts. These shops offer opportunities to find the perfect gift or a mutual treasure to remember your trip by.

Planning Your Stay

When booking The Cottage or one of the 16 guest rooms in the main house at Five Gables Inn, plan well in advance as these intimate accommodations can fill quickly, especially during holidays or long weekends. Consider a midweek stay to fully appreciate the area’s charm without feeling rushed (plus it can be fun to feel like you are playing hooky from work).

Pack appropriately for Maine’s cool weather, but don’t forget your swimsuit for the hot tub. It is a good idea to bring layers for sunny days that can feel warm but then turn to chilly evenings. Consider bringing your favorite movies or board games for entertainment during quiet evenings in. The Cottage also has a shuffleboard table if you are feeling competitive.

The Magic of Winter by the Coast

Boothbay Harbor in winter offers a different kind of romance – one where snuggling close isn’t just enjoyable but necessary, where sharing warmth becomes a metaphor for sharing love, and where the quiet of the season allows couples to truly focus on each other.

The Cottage at Five Gables Inn provides the perfect backdrop for this intimate celebration. Between soaks in the hot tub overlooking the harbor and evenings spent by the crackling fireplace, couples can create memories that will warm their hearts long after they return home.

This winter, consider escaping to this coastal Maine haven. In Boothbay Harbor, you’ll find that the chill in the air only serves to bring hearts closer together, creating the perfect setting for celebrating your love story.