Calendar View
  • Dates
    Any
  • Occupancy
    Any
    - +
    - +
    - +
  • Rooms
    Any
  • Price Range
    Any
  • Amenities
    Any
  • List
  • Map
  • Calendar

Harpswell Vacation Rentals

1 - 36 of 36 rentals
  PrevNext  
Mon 24 Apr Tue 25 Apr Wed 26 Apr Thu 27 Apr Fri 28 Apr Sat 29 Apr Sun 30 Apr Mon 1 May Tue 2 May Wed 3 May Thu 4 May Fri 5 May Sat 6 May Sun 7 May Mon 8 May Tue 9 May Wed 10 May
Harpswell Bay House - Harpswell, ME Vacation Rental

Harpswell Bay House

Harpswell, ME
3 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
Barrett's Watch Cottage and Retreat - Boothbay Harbor, ME Vacation Rental
- - - - - - - 215 225 225 225 270 270 225 225 225 225
Sebasco Serenity - Phippsburg, ME Vacation Rental

Sebasco Serenity

Phippsburg, ME
1 Bed 1 Bath Sleeps 3
- - - - - - - 85 90 90 90 115 115 90 90 90 90
Muirgen Enchantment by the Sea - Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
On The Edgecomb - Edgecomb, ME Vacation Rental

On The Edgecomb

Edgecomb, ME
3 Bed 3 Bath Sleeps 6
130 130 130 130 170 170 135 155 155 155 155 195 195 155 155 155 155
Woodland - Portland, ME Vacation Rental

Woodland

Portland, ME
3 Bed 1.5 Bath Sleeps 8
- 99 99 90 - - - - - - - - - 99 115 115 115
Peg's Pond House - Trevett, ME Vacation Rental

Peg's Pond House

Trevett, ME
3 Bed 2 Bath Sleeps 7
99 115 115 99 - - 130 135 135 135 135 195 195 135 135 135 135
Garravale - Boothbay Harbor, ME Vacation Rental

Garravale

Boothbay Harbor, ME
4 Bed 2 Bath Sleeps 8
- - - - - - - - - - - - - 140 150 150 150
Sunset Circle - East Boothbay, ME Vacation Rental

Sunset Circle

East Boothbay, ME
3 Bed 3 Bath Sleeps 6
115 115 115 115 145 145 120 155 155 155 155 195 195 145 - - -
The Oar House - Wiscasset, ME Vacation Rental

The Oar House

Wiscasset, ME
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Linekin Bay Lookout  - East Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Frosty Glen, a Southport Island Retreat - Southport, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Popham Pines Beach Retreat - Phippsburg, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Robinhood Retreat at Georgetown - Georgetown, ME Vacation Rental
- - - - - - - - - - - - - - - - -
The Atlantic House at Ocean Point - East Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
The 1909 Cottage - Boothbay Harbor, ME Vacation Rental

The 1909 Cottage

Boothbay Harbor, ME
7 Bed 1.5 Bath Sleeps 14
- - - - - - - - - - - - - - - - -
Bufflehead Cove  - Boothbay, ME Vacation Rental

Bufflehead Cove

Boothbay, ME
3 Bed 2.5 Bath Sleeps 7
- - - - - - - - 130 135 135 195 195 135 135 135 135
Cabin on the Shore - East Boothbay, ME Vacation Rental

Cabin on the Shore

East Boothbay, ME
2 Bed 1 Bath Sleeps 4
- - - - - - - - - - - - - - - - -
Towns-End Cottage - Boothbay Harbor, ME Vacation Rental

Towns-End Cottage

Boothbay Harbor, ME
3 Bed 1 Bath Sleeps 6
- 99 99 99 135 135 99 90 90 90 90 135 135 90 90 90 90
Sunshine Cottage - East Boothbay, ME Vacation Rental

Sunshine Cottage

East Boothbay, ME
2 Bed 2.5 Bath Sleeps 6
- - - - - - - 99 115 115 115 160 160 115 115 99 -
The Shore Road Escape - Cape Elizabeth, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Sebenoa Retreat at Sprucewold - Boothbay Harbor, ME Vacation Rental
- - - - - - - - 99 99 99 115 115 99 99 99 99
Willard Square Getaway - South Portland, ME Vacation Rental
- - - - - - - - - - - - - - 135 140 140
River View Suite - Edgecomb, ME Vacation Rental

River View Suite

Edgecomb, ME
3 Bed 3 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Captain's Cottage - Boothbay Harbor, ME Vacation Rental

The Captain's Cottage

Boothbay Harbor, ME
3 Bed 1.5 Bath Sleeps 5
- - - - - - - - - - - - - - - - -
Boothbay Beauty - Boothbay Harbor, ME Vacation Rental

Boothbay Beauty

Boothbay Harbor, ME
3 Bed 1 Bath Sleeps 6
- - - - - - - 150 150 150 150 170 170 150 150 150 150
Willard Square Overlook - South Portland, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Willard Retreat - South Portland, ME Vacation Rental

Willard Retreat

South Portland, ME
2 Bed 1 Bath Sleeps 6
- - - - - - - - - - - - - - - - -
The Ocean Street Barn House - South Portland, ME Vacation Rental
99 99 99 99 125 125 99 135 - - - - - - - - -
Sheepscot Harbour Waterview Suite - Edgecomb, ME Vacation Rental
70 70 70 70 99 99 75 - - - - - - - - - -
The Summit Boathouse - Boothbay Harbor, ME Vacation Rental
- - - - - - - - - - - - - - - - -
The Retreat at Seal Cove  - West Bath, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Ocean Breeze at Boothbay Harbor - Boothbay Harbor, ME Vacation Rental
- - - - - - - - - - - - - - - - -
Barters Island Waterfront Cottage - Boothbay, ME Vacation Rental
- - - - - - - - - - - - - - - - -
The Notebook - Boothbay Harbor, ME Vacation Rental

The Notebook

Boothbay Harbor, ME
4 Bed 2.5 Bath Sleeps 7
- - - - - - - - - - - - - - - - -
Sheepscot Harbour Lodge Suite - Edgecomb, ME Vacation Rental
- - - - - - - - - - - - - - - - -

About Harpswell

To explore the northeastern reaches of Casco Bay is to discover a narrow scenic peninsula, a collection of more than 200 tranquil islands, and nearly 216 miles of shoreline that comprise the coastal community of Harpswell. As the American author Harriet Beecher Stowe once wrote, this town of just under 5,000 residents is "of more varied and singular beauty than can ordinarily be found on the shores of any land." It's a place full of history, natural beauty, and open seascapes, and you'll feel its wonder all around you at our Harpswell vacation homes. 

Where is Harpswell, ME?

With borders that encompass the peninsula of Harpswell Neck, Sebascodegan Island (known locally as Great Island), Orr's Island, Bailey Island, and 200 smaller islands accessible only by boat, Harpswell sits in Casco Bay just 40 miles east of historic downtown Portland. The peninsula and its three main islands (which are connected by bridges) are only 13 miles south of Bowdoin College in Brunswick, 17 miles south of Bath, and 20 miles southeast of the famous outlets in Freeport. 

Things to Do in Harpswell, ME

For more than a century, Harpswell has welcomed visitors in search of ocean views, working harbors, public trails and marinas, and quiet natural splendor. Set sail on your own craft from one of the town's 11 public landings, marinas, and boat launches, or book a charter excursion with ALERT Windjammer Cruises, H2Outfitters, or Sail Casco to see the gorgeous coastline from the water.

Thanks to the town's cooperation with the Harpswell Heritage Land Trust, our Harpswell vacation rentals enjoy direct access to beautiful walking trails, serene nature preserves, and pristine beaches. Take a walk along the 2.3-mile Cliff Trail to soak in views that overlook Long Reach, or stroll the easy half-mile Giant's Stairs Trail to admire spectacular vistas of eastern Casco Bay. Johnson Field at Mackerel Cove is also a beloved local landmark for its picturesque Bailey Island harbor, its lovely beach, and its ideal setting for picnicking and kayaking.

View the islands through the eyes of local painters at the Sebascodegan Artists Gallery, or catch a summer evening concert with a crowd of locals at Mitchell Field's Bandstand by the Sea.

Day Trips from Harpswell, ME

While Harpswell is known for its peace and quiet, the beauty of this bayfront community is its close proximity to Maine's largest city, one of its most respected colleges, and a bastion of the state's shipbuilding history.

Take a short and scenic drive to reach the old port of Portland, a thriving and artistic city that boasts some of New England's most charming streets and exciting cuisine. Grab morning pastries at Standard Baking Co., savor a lunchtime lobster roll at Fishermen's Grill, and taste the divine local bounty at Eventide Oyster Co.

Guarding the northern reaches of Harpswell Neck is the shopping mecca of Freeport (the flagship location of the iconic outfitter L.L. Bean), while nearby Brunswick has gained fame as the home of Bowdoin College. You'll also be just 18 miles from the Maine Maritime Museum in the historic town of Bath on the Kennebec River. 

The countless wonders of Midcoast Maine await - plan an escape to our Harpswell vacation homes for an experience you'll never forget.

Photo Credit: K.ristin via Flickr

  • Searching ...
  • 36 of 36
No results in this area. Move map or change filters for more rentals.
  • More Map
  • Less Map
Search Here