Vacation rentals in Westport

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Top-rated vacation rentals in Westport

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Guest favorite

Home in Edgecomb

4.99 out of 5 average rating, 119 reviews

Cozy Lodge Meets Mid Century Hideaway

Ah where to begin with my cozy hideaway! If you're looking for a quiet & nurturing space to curl up in and be creative, relax after a day of exploring, or work remotely, this is the home for you. The house sits on 2 acres and is surrounded by trees. The upper floor features two bedrooms, both with casper mattresses, a full bath, and thirteen-foot ceilings. The design of the lower level's living space is warm and inviting; a Maine retreat close to all the amenities The Midcoast has to offer.

Apr 21 – 28

R3,084 ZAR per night

Guest favorite

Apartment in Edgecomb

4.91 out of 5 average rating, 297 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

Feb 5 – 12

R1,935 ZAR per night

Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 430 reviews

Harpswell Studio on Waterview Property! Lobster!

Attached Cottage Style Studio! Clean, comfy, spacious, colorful and bright! Easy access to Harpswell’s 216 miles of coastline via coastal trails, lovely side roads, small beaches and preserves. Too many trails to count in the surrounding area! Fresh lobster and seafood! Two spectacular state parks with expansive beaches within a scenic 35 minute drive! Just 45 minutes (33 miles) to Coastal Maine Botanical Gardens! Saturday check-in may be available before mid June. Please message us.

Nov 22 – 29

R2,629 ZAR per night

Guest favorite

Guest suite in Woolwich

4.92 out of 5 average rating, 187 reviews

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, comfortable queen bedroom, Wifi; fully equipped kitchenette; spacious bathroom with large jacuzzi tub and separate walk-in shower. Roomy sitting/dining area opens out onto deck with Adirondack chairs; table and grill. Large smart TV. Fast Wi-Fi. Firepit.

Jul 8 – 15

R1,985 ZAR per night

Guest favorite

Farm stay in Westport Island

4.82 out of 5 average rating, 108 reviews

| Westport Island 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.

Mar 3 – 10

R5,846 ZAR per night

Guest favorite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 326 reviews

The Cottage at the McCobb House

Freshly renovated inside and out, the cottage is your private Maine camp. Located on an acre and a half of wooded grounds, and surrounded by forest, the cottage feels secluded, but it’s only a mile to the restaurants, shops, and waterfront attractions of bustling Boothbay Harbor. With hiking trails in the Pine Tree Preserve that adjoins the property and the Lobster Cove Meadow Preserve a five minute walk up the road, you can also explore nature and enjoy the solitude of the woods.

Feb 4 – 11

R3,150 ZAR per night

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 402 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Stay in our custom designed tree dwelling w/ wood-fired cedar hot tub up among the trees! This unique structure is perched atop a 21-acre wooded hill sloping to water views. Enjoy stunning views from the King size bed through a wall of windows. Located in a classic coastal Maine village w/ Reid State Park's miles of beaches + famed Five Islands Lobster Co. (See 2 other tree dwellings on our 21 acre property listed on AirBnb as "Tree Dwelling w/Water Views." See our reviews!).

Dec 14 – 21

R6,492 ZAR per night

Guest favorite

Guesthouse in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

Charming cottage on a beautiful island near marina, beaches, restaurants, and hiking trails. Wonderful mid-coast Maine location for lots of possibilities for outdoor adventures, antiquing, visiting art galleries and shops, and enjoying delicious cuisine. The cottage has everything you need for a peaceful getaway. Decorated with natural elements and local art pieces to get you in the mood for this beautiful location.

Jul 16 – 23

R2,388 ZAR per night

Guest favorite

Guesthouse in Boothbay Harbor

5.0 out of 5 average rating, 225 reviews

The Sparrow’s Nest Charming Country Cottage

The Sparrow's Nest is on a quiet country road approximately 5 miles from downtown Boothbay Harbor. The Sheepscot River, it's coves and nature trails are close by. Enjoy the beautiful and peaceful 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 marveling at the night sky.

Sep 18 – 25

R8,348 ZAR per night

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

Jan 21 – 28

R1,269 ZAR per night

Guest favorite

Guest suite in Bath

4.97 out of 5 average rating, 202 reviews

Historical Bath ME. Rated top 10 charming NE town.

Private entrance to second floor bedroom suite with private full bath & small snack station. No shared living space, completely private with limited amenities offered-please review. Quiet neighborhood within walking distance to historical downtown Bath for dining, entertainment and waterfront.

Jun 17 – 24

R2,622 ZAR per night

Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

Oct 17 – 24

R1,574 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westport vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Westport's top sights

Coastal Maine Botanical Gardens163 locals recommend

Montsweag Farm Restaurant18 locals recommend

Monkey C Monkey Do11 locals recommend

Wiscasset Antiques Mall7 locals recommend

Boothbay Region Land Trust23 locals recommend

Porters Preserve11 locals recommend

Other great vacation rentals in Westport

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 344 reviews

Waterfront Guest House on the Maine Coast

Oct 28 – Nov 4

R3,255 ZAR per night

Guest favorite

Apartment in Damariscotta

4.83 out of 5 average rating, 156 reviews

President Polk Suite, Downtown Damariscotta

Dec 25 – Jan 1

R1,991 ZAR per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Nov 12 – 19

R3,082 ZAR per night

Guest favorite

Guest suite in Bowdoinham

4.96 out of 5 average rating, 101 reviews

Sunny riverside carriage house

May 26 – Jun 2

R2,510 ZAR per night

Guest favorite

Apartment in Damariscotta

4.92 out of 5 average rating, 253 reviews

Fernald's Backside

Nov 30 – Dec 7

R2,250 ZAR per night

Guest favorite

Cabin in Edgecomb

4.87 out of 5 average rating, 858 reviews

The Highland Cottage on Sheepscot

Oct 29 – Nov 5

R2,874 ZAR per night

Guest favorite

Apartment in Woolwich

5.0 out of 5 average rating, 26 reviews

Cozy, MidCoast Apartment

Jan 20 – 27

R2,461 ZAR per night

Guest favorite

Guest suite in Wiscasset

5.0 out of 5 average rating, 12 reviews

Birch Point at Cushman Cove- Private/Entire Suite

May 30 – Jun 6

R2,823 ZAR per night

Show all

Quick stats about vacation rentals in Westport

Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
1.7K reviews

Frequently Asked Questions

Do house rentals in Westport have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Westport. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Westport have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Westport. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Westport?
Four-legged friends are welcome in Westport. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Westport?
Experience the best of Westport with our cottage rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Westport have wifi?
Absolutely! We offer over 30 house rentals with wifi in Westport. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Westport?
Yes! Work meets play with ease at over 30 vacation rentals in Westport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Westport?
Westport has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Westport have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Westport. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Westport

Top-rated vacation rentals in Westport

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Westport vacation rentals

Stay near Westport's top sights

Other great vacation rentals in Westport

Guesthouse in South Bristol

Apartment in Damariscotta

Cottage in Topsham

Guest suite in Bowdoinham

Apartment in Damariscotta

Cabin in Edgecomb

Apartment in Woolwich

Guest suite in Wiscasset

Quick stats about vacation rentals in Westport

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Westport have a kitchen?

Do cottage rentals in Westport have free parking?

Are there pet-friendly vacation rentals in Westport?

How much does it cost to stay in cottage rentals in Westport?

Do house rentals in Westport have wifi?

Are there vacation rentals with a dedicated workspace in Westport?

Are there family-friendly vacation rentals in Westport?

Do house rentals in Westport have air conditioning?

Destinations to explore