Harpswell vacation rentals

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Top-rated vacation rentals in Harpswell

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Guest favorite

Guesthouse in Harpswell

4.95 out of 5 average rating, 431 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.

May 10 – 17

G$27,955 GYD per night

Guest favorite

Loft in Brunswick

4.97 out of 5 average rating, 180 reviews

The Douglas Park Loft

The loft is a 20 X 20 space above our detached garage. Wide pine floors. 7 windows facing. Optimal for a couple. Sleep sofa is 70" x 54" so suitable for 1 adult or 2 children/teens. Sunny room w/room darkening shades. Radiant floor in the bathroom. Smart TV. Low radiation WiFi. Ethernet jack. Heat pump for heat or AC. Large under counter fridge w/out freezer but we have one in the garage. Two burner infrared cook-top. Toaster oven, Hot H2O kettle & coffee maker. Kitchen is ready for cooking.

Mar 29 – Apr 5

G$25,352 GYD per night

Guest favorite

Guest suite in Brunswick

4.93 out of 5 average rating, 322 reviews

Private Guest Suite in Historic Downtown Brunswick

Welcome to the barn at 64 Federal! Enjoy this private guest suite, featuring its own entry, sitting room, bedroom, private bath, and laundry in a separate wing of this 1838 Greek Revival home. Plenty of light and heat pump/AC. Just two blocks to Bowdoin College and downtown Brunswick. Home on the National Historic Register and directly across from the Harriet Beecher Stowe House. Quiet family of four live in main wing of the house. Suite includes queen bed, pull-out couch and smart TV.

May 8 – 15

G$31,968 GYD per night

Superhost

Cottage in Harpswell

4.9 out of 5 average rating, 124 reviews

Classic Maine Cottage - dock, sauna & kayaks

The Perfect Maine Cottage! On the edge of the ocean, carefully preserved with traditional details. Charming, open floor plan, with a wall of windows to the ocean. Sunny large wrap-around deck and screen porch creates beautiful outside spaces to enjoy. Perfect for listening to waves and watch lobstermen pull up their traps. Cathedral ceilings and Scandinavian design gives the cottage an exclusive feeling. Gentle stairs lead to the private deep water dock for all kinds of boating.

Oct 3 – 10

G$102,462 GYD per night

Guest favorite

Cabin in Freeport

4.98 out of 5 average rating, 469 reviews

Cozy Cottage-Near Harbor & Park

Bailiwick Cottage is a cozy, private cottage that looks south down Freeport (Harraseeket) Harbor in Freeport, ME. It is a 4 season accommodation that is close to Freeport shopping, Portland eating, and the Adventure Schools of LL Bean. The cottage sits approximately 50 yards from our main house, has its own parking space and patio, and offers the ability to come and go as you wish. We have had 12 honeymoons in the cottage. Freeport Registration # STRR-2022-59

May 14 – 21

G$32,625 GYD per night

Guest favorite

Guest suite in Brunswick

4.93 out of 5 average rating, 314 reviews

Art House Gallery guest suite

Welcome come stay at our 2 Bedroom guesthouse/duplex convenient to everything,walking distance to downtown 15 minutes to Freeport 25 minutes to Portland.smoke-free,private entrance ,WiFi,washer/dryer,full kitchen,pet friendly,40"TV smart tv with Netflix and Hulu, 5 minutes to Bowdoin College! Free eggs from our chickens included! And while in season help yourself to our vegetable garden. Fire pit area grill and outdoor dining area. We recycle and compost!

Mar 15 – 22

G$24,267 GYD per night

Guest favorite

Apartment in Freeport

4.91 out of 5 average rating, 195 reviews

1000 sq. ft. 1BR+ Apt Close to Town & Nature

This very spacious and light filled apartment has beautiful views of a marsh and the headwaters of the Harraseeket River. It is also across the street from a 100+ acre bird sanctuary. There is a queen bed in the bedroom, a twin in the large living room, and a twin in a small nook under the eaves off of the kitchen. You can put kayaks in across the street and it is a short 20 minute walk into downtown Freeport. Great year-round location.

Feb 23 – Mar 2

G$23,138 GYD per night

Guest favorite

Guest suite in Freeport

4.97 out of 5 average rating, 118 reviews

Solar Suite surrounded by Nature

Solar suite on conservation property offers peaceful getaway. Large sitting room furnished with contemporary sofa, reading area, bedroom nook with natural latex Queen mattress on Japanese platform, kitchen island/toaster oven, mini fridge, dishes, silverware, linen napkins (please note this is not a full kitchen for preparing meals) private bath/shower. On the lower level of our home with private entrance. Cedar hot tub available.

Dec 4 – 11

G$25,447 GYD 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.

Aug 4 – 11

G$25,970 GYD per night

Guest favorite

Apartment in Harpswell

4.94 out of 5 average rating, 172 reviews

Comfortable studio apartment in quiet location

Peaceful, rural second story studio apartment. Near Middle Bay in beautiful Harpswell, Maine. Enjoy our farmer's porch or walks to the shore deck to look out over the water and enjoy a sunset or go the the shore for a swim in summer. Short distance to Brunswick and Bowdoin College, local restaurants. The host also teaches porcelain doll making. You could learn to make porcelain dolls while enjoying the Maine coast.

Sep 16 – 23

G$31,627 GYD per night

Guest favorite

Home in Harpswell

4.98 out of 5 average rating, 174 reviews

Waterfront Cottage On Basin Cove - Amazing Sunsets

Bright, airy cottage right on Basin Cove in Harpswell Maine. Cool breezes with pristine views, especially for the sunsets over the cove. At the end of Harpswell Neck, so it feels like you're far away, but still only an hour from Portland, 1/2 hour from Freeport & 15 minutes from Brunswick. Use it as your hub to explore Midcoast Maine or hunker down and enjoy the screened in porch after a swim in the cove.

Mar 11 – 18

G$60,110 GYD per night

Guest favorite

Guest suite in Freeport

4.95 out of 5 average rating, 197 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

May 18 – 25

G$14,519 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Harpswell vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Harpswell's top sights

Wolfe's Neck Woods State Park123 locals recommend

Wolfe's Neck Oceanfront Camping5 locals recommend

Cook's Lobster & Ale House61 locals recommend

Dolphin Marina & Restaurant81 locals recommend

Land's End Gift Shop41 locals recommend

Erica's Seafood29 locals recommend

Other great vacation rentals in Harpswell

Guest favorite

Cottage in Edgecomb

4.91 out of 5 average rating, 106 reviews

Spectacular Water View Cottage

Dec 19 – 26

G$27,387 GYD per night

Guest favorite

Cottage in Topsham

4.95 out of 5 average rating, 212 reviews

Cozy waterfront home on Merrymeeting Bay.

Oct 24 – 31

G$33,519 GYD per night

Guest favorite

Cottage in Pownal

4.99 out of 5 average rating, 323 reviews

Upscale Timber-Frame Cottage, Shop/Dine/Hike/Bike

Jan 5 – 12

G$56,900 GYD per night

Guest favorite

Cottage in Boothbay Harbor

4.98 out of 5 average rating, 327 reviews

The Cottage at the McCobb House

Oct 24 – 31

G$34,260 GYD per night

Guest favorite

Cottage in Edgecomb

4.97 out of 5 average rating, 177 reviews

Charming Cottage With Spectacular Water View

Oct 16 – 21

G$43,885 GYD per night

Guest favorite

Cottage in Scarborough

4.97 out of 5 average rating, 161 reviews

Bright, clean, private cottage near Higgins Beach!

Mar 24 – 31

G$33,021 GYD per night

Guest favorite

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

Dec 3 – 10

G$30,230 GYD per night

Guest favorite

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Oct 6 – 13

G$30,051 GYD per night

Show all

Other great vacation rentals in Harpswell

Guest favorite

Apartment in Orr's Island

4.91 out of 5 average rating, 109 reviews

Shore House, Posey Unit - Ocean Front Property

Nov 23 – 30

G$37,060 GYD per night

Guest favorite

Guest suite in Brunswick

4.93 out of 5 average rating, 113 reviews

Brunswick Bungalow Efficiency

Oct 1 – 8

G$21,445 GYD per night

Guest favorite

Home in Freeport

4.94 out of 5 average rating, 206 reviews

The Outlet House, Comfortable Cottage

Oct 13 – 20

G$31,309 GYD per night

Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Sep 23 – 30

G$21,254 GYD per night

Guest favorite

Home in Edgecomb

4.95 out of 5 average rating, 403 reviews

Sheepscot Harbour Cottage/waterview

Apr 8 – 15

G$30,293 GYD per night

Guest favorite

Apartment in Freeport

5.0 out of 5 average rating, 130 reviews

Cozy Maine Barn Hideaway- 2nd Floor Apartment

May 25 – Jun 1

G$38,198 GYD per night

Guest favorite

Treehouse in Georgetown

4.98 out of 5 average rating, 403 reviews

Modern Tree Dwelling w/Water Views+Cedar Hot Tub

Dec 14 – 21

G$70,609 GYD per night

Guest favorite

Yurt in Chebeague Island

4.97 out of 5 average rating, 101 reviews

Yurt on Chebeague Island

Feb 6 – 13

G$25,936 GYD per night

Show all

Quick stats about vacation rentals in Harpswell

Total rentals
280 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
110 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
7K reviews
Nightly prices starting at
G$10,424 GYD before taxes and fees

Frequently Asked Questions

What types of vacation rentals are available in Harpswell?
Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Harpswell. From over 70 cottage rentals to over 140 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.
Are there vacation rentals with a dedicated workspace in Harpswell?
Yes! Work meets play with ease at over 130 vacation rentals in Harpswell featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Harpswell?
Four-legged friends are welcome in Harpswell. Choose from more than 110 vacation rentals for guests traveling with pets.
How much does it cost to stay in cottage rentals in Harpswell?
Experience the best of Harpswell with our cottage rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Harpswell have self check-in?
Absolutely! We offer over 20 cottage rentals with self check-in in Harpswell. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Harpswell have a bbq area?
Absolutely! We offer over 50 cottage rentals with a bbq area in Harpswell. Enjoy a tailored experience with all the comforts you desire.
Do cottage rentals in Harpswell have wifi?
Absolutely! We offer over 70 cottage rentals with wifi in Harpswell. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Harpswell?
Harpswell has more than 60 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Harpswell vacation rentals

Top-rated vacation rentals in Harpswell

Vacation rentals for every style

Cottages

Apartments

Houses

Popular amenities for Harpswell vacation rentals

Stay near Harpswell's top sights

Other great vacation rentals in Harpswell

Cottage in Edgecomb

Cottage in Topsham

Cottage in Pownal

Cottage in Boothbay Harbor

Cottage in Edgecomb

Cottage in Scarborough

Cottage in Rockport

Cottage in Owls Head

Other great vacation rentals in Harpswell

Apartment in Orr's Island

Guest suite in Brunswick

Home in Freeport

Apartment in Boothbay

Home in Edgecomb

Apartment in Freeport

Treehouse in Georgetown

Yurt in Chebeague Island

Quick stats about vacation rentals in Harpswell

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What types of vacation rentals are available in Harpswell?

Are there vacation rentals with a dedicated workspace in Harpswell?

Are there pet-friendly vacation rentals in Harpswell?

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

Do cottage rentals in Harpswell have self check-in?

Do cottage rentals in Harpswell have a bbq area?

Do cottage rentals in Harpswell have wifi?

Are there family-friendly cottage rentals in Harpswell?

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