
Vacation rentals in Westport Island
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Top-rated vacation rentals in Westport Island
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Tiny A-Frame Romantic Getaway
Camp Lupine is a brand new Luxury 400 sq ft Tiny A-Frame tucked away on a private wooded lot with a small stream just a quarter mile off Coastal Route 1. With Historic Wiscasset, Booth Bay, Bath, Freeport, and Portland all at your fingertips, it’s the perfect romantic getaway. Spend your days exploring coastal Maine and your nights soaking in the hot tub with a glass of Malbec. Stay for a while and explore the growing restaurant scene in Wiscasset and the entire Midcoast region. See you soon!

1820s Maine Cottage with Garden
Enjoy a cozy shipbuilder's cottage in Bath, Maine. This quaint apartment attached to a family home has its own entrance and contains a bedroom, a bathroom, a kitchen, and a living room with antique details that reflect its 200-year old history. Only a 15-minute walk to historic downtown Bath, a 3-minute drive to Thorne Head Preserve, and a 25-minute drive to Reid State Park and Popham Beach. Come appreciate everything MidCoast Maine has to offer! PLEASE NOTE: This apartment has steep stairs!

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.

25 Middle: Two floor loft w. water view -sleeps 5
A private apartment on the second and third floor of an historic house located in the heart of Wiscasset village. Featuring a bird’s eye views of the harbor and surrounded by lovely gardens.Stroll to restaurants, waterfront, antique shops, historic homes & gardens. Ideal base for touring Maine attractions. Full kitchen, five other rooms including two full baths.A//C in bedroom suite and 3rd floor loft space.Central yet private. Tastefully decorated .Not suitable for children younger than 12.

The Stilt House
Once the island Trading Post (in the 1820's) now serves as a private retreat on Westport Island. The whole property has been listed on the National Register of Historic Places since 1982. The building is nestled at the water's edge, half on land and half on stilts over the tidal waters of the Sheepscot River. The property has its own private deck, island, rocky beach, trails and hammock. This is an old structure - over 200 years old! A great piece of history and an absolute oasis.

Serenity, Privacy, Clean and Bright
This large studio can be rented by the week only June - September. A high ceiling, many windows and skylights give this space a feeling of spaciousness. On a private road. A short walk takes you to the Damariscotta River. Perfect for artists, writers and those looking for a retreat space. 10 miles away are great cafes, stores, a movie theater, a health food store "better than Whole Foods", a lighthouse and a beautiful beach. Close by are countless spectacular walking trails.

Renovated home with amazing waterfront views
Welcome to Dancing Pines Cottage! We are located across from West Harbor Pond with beautiful water views in each room. Relax on the deck or bbq on the patio or take a short drive into charming Boothbay Harbor town for lobster rolls. We have three bedrooms and a den/office and 2 full bathrooms and can accommodate up to 7 guests. The house is private and has ample parking. One week rentals for June, July, and August (Saturday-Saturday). We accept either one dog or one cat.

Near Beach+Cedar Sauna+Outdoor Shower+Pond+FirePit
Unwind at your own studio cabin with forest views, private sauna & pond! * New Private Cedar & Glass Barrel Sauna * Minutes to Reid State Park Beach & 5 Island🦞 * Fire Pit * Outdoor Shower * Rain Shower & Heated Bathroom Floor * AC/Heat * TV & Record Player w/Vinyl * Fast Wifi *Spruce Studio is one of two cabins on 8 acres right down the road from one of the best beaches in Maine! The cabins are 150ft. apart & separated by a privacy screen and natural landscaping.

Panoramic Water Views on the Sheepscot
From our living room a wall of windows take in the expansive views of Barter's Island upward to the ocean. Relax on the sunny deck, listen to the birds and lobster boats and watch the seals on the ledge at low tide. Take a walk for breathtaking scenic views of the Sheepscott river. Bring your books, bikes and kayaks. Westport Island offers several preserves for hiking, a local brewery and is a central location to visit many nearby midcoast sights and activities.

SNOW SWEET, A Yurt for All Seasons
Snow Sweet at The Appleton Retreat is very private, check out the Trail Map. This contemporary yurt faces the Field of Dreams and has a nice view of Appleton Ridge. It features a private therapeutic hot tub on the deck, a fire pit, and fast wifi. The Appleton Retreat encompasses 120 acres hosting six unique retreats. To the south is the Pettengill Stream, a resource protected area. To the north is the Nature Conservancy's 1300 acre reserve.

Private Guest Apartment with separate entrance.
Your perfect base for discovering all the wonderful places Midcoast Maine has to offer. Located on a peaceful wooded lot, this one bedroom apartment sits on the ground floor of our 2-story home. Separate private deck entry with parking. sitting room with a dining table that looks out onto the deck, queen bedroom, private bathroom with jetted tub and separate shower, fully equipped kitchenette; NEW FURNACE-quiet and efficient.

The Sparrow’s Nest Charming Country Cottage
The Sparrow's Nest is located on a country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful country surroundings, gardens, and the miracle of nature. What a delight to wake up to the sound of birdsong while enjoying a cup of local coffee, or sitting by the outdoor fire sipping wine and taking in the beautiful night sky.
Popular amenities for Westport Island vacation rentals
Stay near Westport Island's top sights
Other great vacation rentals in Westport Island

The Treehouse Studio

Spacious 1 Bedroom Cottage Close to Everything 1

Private Shorefront | Firepit | Kayaks & Canoe

Welcome to Morning View!

Seahorse Shores of Wiscasset, ME

The Nest on Sawyers Island

Five Islands Waterfront Retreat

Guesthouse on Sheepscot River
When is the best time to visit Westport Island?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$37,629 GYD | G$41,601 GYD | G$40,765 GYD | G$55,817 GYD | G$42,437 GYD | G$46,618 GYD | G$47,037 GYD | G$52,263 GYD | G$52,263 GYD | G$51,218 GYD | G$53,308 GYD | G$51,218 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 6°C | 12°C | 17°C | 21°C | 20°C | 16°C | 9°C | 3°C | -2°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Westport Island?
Westport Island has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in cottage rentals in Westport Island?
Experience the best of Westport Island with our cottage rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly house rentals in Westport Island?
Four-legged friends are welcome in Westport Island. Choose from more than 20 house rentals for guests traveling with pets.
Are there house rentals with a dedicated workspace in Westport Island?
Yes! Work meets play with ease at over 20 house rentals in Westport Island featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do hotel rentals in Westport Island have air conditioning?
Absolutely! We offer over 10 hotel rentals with air conditioning in Westport Island. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westport Island have a kitchen?
Absolutely! We offer over 40 house rentals with a kitchen in Westport Island. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Westport Island have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Westport Island. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Westport Island have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Westport Island. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Westport Island

Total vacation rentals
Explore 90 vacation rentals in Westport Island

Nightly prices starting at
Westport Island vacation rentals start at G$14,634 GYD per night before taxes and fees

Verified guest reviews
Over 2,580 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
90 of Westport Island vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Westport Island rentals

4.9 Average rating
Westport Island stays are highly rated by guests—averaging 4.9 out of 5!
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- Sebago Lake
- Popham Beach, Phippsburg
- Scarborough Beach
- Willard Beach
- Pemaquid Beach
- Popham Beach State Park
- East End Beach
- Pemaquid Point Lighthouse
- Wolfe's Neck Woods State Park
- Coastal Maine Botanical Gardens
- Crescent Beach State Park
- Hills Beach
- Funtown Splashtown USA
- Palace Playland
- The Camden Snow Bowl
- Fortunes Rocks Beach
- Rockland Breakwater Light
- Portland Museum of Art
- Maine Maritime Museum
- Bradbury Mountain State Park
- Farnsworth Art Museum
- Camden Hills State Park
- Bug Light Park
- Aquaboggan Water Park





