Holiday rentals in Windsor

Oceanfront Home Acadia-Camden -Belfast

Relax with the whole family at this peaceful place just one hour from Acadia National Park. Centrally located in Mid Coast Maine, this home is the perfect location to spend time by the salt water or take day trips to the surrounding attractions. Small private beach and 3 other public beaches nearby. Kayak right in front of the property or relax by the wood fire pit and look out onto the water. This home offers everything you will need to make for a great escape from the demands of daily life.

Waterfront Gem walkable to Restaurants!

Waterfront Oasis on Pettingill Pond. You couldn't get any closer to the water, it's steps away. There are 3 Kayaks, and a paddleboat, firepit and dock for guest use! This a great spot for swimming and watersports! This home has been newly renovated, the effect results in a simple, stylish, comfortable space for guests to enjoy. Walk to Franco's Bistro for from Scratch Italian food, or Bob's Seafood for a fish taco! This is a piece of paradise on sweet Pettingill Pond in the heart of Windham.

Tailwinds - Upscale Oceanfront! Stunning Views!

Welcome to Tailwinds in East Boothbay, where you will enjoy stunning sunsets over Linekin Bay from the comfort of this beautifully updated home. Formerly a B&B, this is a perfect place to gather frinds and family with en-suite baths 2 living rooms and a large porch. You will also find all new beds and furniture, luxurious 100% cotton linens, and AC window units in the bedrooms. Located between downtown Boothbay Harbor and Ocean Point, this is a gorgeous spot for your next family vacation!

Cottage by the sea private oceanfront shoreline

Breathtaking oceanfront private cottage. Spiral staircase to second floor bedroom. Sliding glass doors open to wrap-around deck and lawn that slopes to Ocean. 300 + feet of deep water frontage. Separated from lawn by broad rock ledge. Perfect spot for sunbathing or having a campfire in the evening. Enjoy your morning coffee watching lobster and sailboats in the Mussel Ridge Channel. Unbelievable and peaceful views out to ocean and north to the Camden Hills. Unparalleled views everywhere.

Adorable cottage 5 minute walk from downtown

Newly custom renovated 1 BR, 2 floor cottage 5 minute walk from downtown, 2 minutes from farmers market & bay. Each floor has a balcony for AM coffee/evening drinks. Loft style master BR connecting bathroom, first floor kitchen/living room combo - full (compact) kitchen - Custom woodwork, great design. Bathroom accessible from 2nd Fl BR. (The couch was recently replaced it’s not the one pictured (it’s actually much more comfortable) Crib available upon request No pets No smoking

Milk House

nice little vacation cottage in Dark Harbor, near to everything. queen sized bed, so sleeps up to two in a quiet island location for short or medium term stays. most reasonable amenities provided; hiking or social recommendations are available on request. (Wi-Fi speeds are excellent, although I was not able to use AirB&B's official Wi-Fi measurement option.) *Please be aware, this property is on an island, which must be accessed by boat or ferry, so service can be interrupted.

Cub Cabin- a Peaceful Paradise at Fox Carlton Pond

Welcome to Fox Carlton Pond! Settle into our Cub Cabin surrounded by the beauty of nature at a peaceful resort on our 5 acre private pond alongside the Sandy River. Our Cub Cabin is furnished with a bunk bed (see photos) with a double mattress on the bottom bunk that sleeps 2 and a single mattress on top bunk that sleeps 1. Enjoy walking trails, lawn games, fire pit, pickle ball, use of canoes, kayaks, peddle boat and docks for exploring, fishing and swimming.

Freeport Escape – LLBean | Fire Pit | 3 King | A/C

The Freeport Escape – A charming early 1900s home with modern amenities. Located in the heart of Freeport, walkable to shopping, restaurants, breweries, and the Amtrak station. Set on a private corner lot, enjoy the fire pit, porch grilling, and spacious outdoor area. Cozy up by the indoor fireplace in cooler months. Perfect for families, couples, and friends. 🛏️ 3 King Beds | Family-Friendly | ❄️ A/C | 🔥 Fire Pit | 🪵 Indoor Fireplace 📍 STRR-2022-82

Postcard views, ocean front and idyllic cove

Cozy and comfortable unique home nested on the granite ledge at the mouth of Little River and the open ocean in East Boothbay, Maine. Marvel in glorious views from every window, deck and porch. Soak in the salt water hot tub, light up the evening by the outdoor fireplace or just get lost in the starry night sky. Most of all, enjoy every moment and make lifetime memories!