Holiday rentals near White Head Trail
We found 786 holiday rentals — enter your dates for availability
Choose the right holiday home within easy reach of White Head Trail. Holiday rentals provide the best amenities for your family, friends or furry companion, such as parking and a fireplace. You're sure to find a property to rent that has what everyone needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - White Head Trail
Showing deals for:10 Oct - 17 Oct
Image gallery for Oceanfront, views from every room! Spacious midcoast retreat with private dock
1010 out of 10 rating
Exceptional
(21 reviews)
Oceanfront, views from every room! Spacious midcoast retreat with private dock
Round Pond, ME
8% off
Price is AU$11,021
AU$11,021
AU$1,574 per night
includes taxes & fees
Image gallery for Waterfront. Private. Perfect.
1010 out of 10 rating
Exceptional
(5 reviews)
Waterfront. Private. Perfect.
East Boothbay, ME
6% off
Price is AU$9,578
AU$9,578
AU$1,368 per night
includes taxes & fees
Image gallery for Close to Round Pond Harbor and all that mid-coast Maine has to offer!
1010 out of 10 rating
Exceptional
(14 reviews)
Close to Round Pond Harbor and all that mid-coast Maine has to offer!
Round Pond, ME
8% off
Price is AU$9,168
AU$9,168
AU$1,310 per night
includes taxes & fees
Image gallery for Breathtaking Oceanfront Private Cottage
1010 out of 10 rating
Exceptional
(60 reviews)
Breathtaking Oceanfront Private Cottage
South Thomaston, ME
8% off
Price is AU$2,904
AU$2,904
AU$415 per night
includes taxes & fees
Image gallery for Peaceful Private Wooded House Location Near Ocean
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Peaceful Private Wooded House Location Near Ocean
New Harbor, ME
8% off
Price is AU$4,524
AU$4,524
AU$646 per night
includes taxes & fees
Image gallery for Waterfront. Private. Perfect. 3 bedrooms/3 bathrooms. Plus options for kids.
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Waterfront. Private. Perfect. 3 bedrooms/3 bathrooms. Plus options for kids.
East Boothbay, ME
5% off
Price is AU$10,081
AU$10,081
AU$1,440 per night
includes taxes & fees
Image gallery for Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
1010 out of 10 rating
Exceptional
(11 reviews)
Solitude abounds at this idyllic Southport OCEANFRONT home-5 mins from the beach
Southport, ME
8% off
Price is AU$7,337
AU$7,337
AU$1,048 per night
includes taxes & fees
Image gallery for ' The Castle House' of Rutherfords Island, Christmas Cove
1010 out of 10 rating
Exceptional
(13 reviews)
' The Castle House' of Rutherfords Island, Christmas Cove
South Bristol, ME
12% off
Price is AU$8,325
AU$8,325
AU$1,189 per night
includes taxes & fees
Image gallery for Snowball Hill Cottage - Near Pemaquid Beach & New Harbor Village.
1010 out of 10 rating
Exceptional
(17 reviews)
Snowball Hill Cottage - Near Pemaquid Beach & New Harbor Village.
New Harbor, ME
7% off
Price is AU$2,636
AU$2,636
AU$377 per night
includes taxes & fees
Image gallery for Ocean Front Cottage
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Ocean Front Cottage
Tenants Harbor, ME
13% off
Price is AU$1,779
AU$1,779
AU$254 per night
includes taxes & fees
Image gallery for New home in Boothbay, downtown Boothbay harbor is located about a mile away.
1010 out of 10 rating
Exceptional
(13 reviews)
New home in Boothbay, downtown Boothbay harbor is located about a mile away.
Boothbay, ME
8% off
Price is AU$2,434
AU$2,434
AU$348 per night
includes taxes & fees
Image gallery for Maine Coast House with Spectacular Ocean Views and Beach for Swimming
9.49.4 out of 10 rating
Exceptional
(24 reviews)
Maine Coast House with Spectacular Ocean Views and Beach for Swimming
South Bristol, ME
19% off
Price is AU$4,239
AU$4,239
AU$606 per night
includes taxes & fees
Image gallery for Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
1010 out of 10 rating
Exceptional
(40 reviews)
Premier Cottage, #3, w/NEW ADDITION! Now Sleeps 8, Pets Free
Round Pond, ME
9% off
Price is AU$3,045
AU$3,045
AU$435 per night
includes taxes & fees
Image gallery for Sea Haven at Ocean Point
9.09.0 out of 10 rating
Wonderful
(50 reviews)
Sea Haven at Ocean Point
East Boothbay, ME
8% off
Price is AU$3,131
AU$3,131
AU$447 per night
includes taxes & fees
Image gallery for Friendship Harbor Waterfront Home
1010 out of 10 rating
Exceptional
(27 reviews)
Friendship Harbor Waterfront Home
Friendship, ME
8% off
Price is AU$5,063
AU$5,063
AU$723 per night
includes taxes & fees
Image gallery for Secluded Lakefront Cottage on 5 acres. Very private, family friendly.
1010 out of 10 rating
Exceptional
(53 reviews)
Secluded Lakefront Cottage on 5 acres. Very private, family friendly.
Bremen, ME
8% off
Price is AU$3,646
AU$3,646
AU$521 per night
includes taxes & fees
Image gallery for BOLD OCEANFRONT RETRO GUESTHOUSE IN MID-COAST MAINE! 3/1 WITH PRIVATE DECK.
1010 out of 10 rating
Exceptional
(5 reviews)
BOLD OCEANFRONT RETRO GUESTHOUSE IN MID-COAST MAINE! 3/1 WITH PRIVATE DECK.
Chamberlain, ME
8% off
Price is AU$4,184
AU$4,184
AU$598 per night
includes taxes & fees
Image gallery for Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
1010 out of 10 rating
Exceptional
(11 reviews)
Newly renovated modern guest cottage across from Spruce Point Inn Pet Friendly!
Boothbay Harbor, ME
8% off
Price is AU$3,640
AU$3,640
AU$520 per night
includes taxes & fees
Image gallery for Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
1010 out of 10 rating
Exceptional
(97 reviews)
Peaceful Lake Waterfront! Automatic backup Generator! Full Kitchen! Heat & A/C
Boothbay Harbor, ME
8% off
Price is AU$3,387
AU$3,387
AU$484 per night
includes taxes & fees
Image gallery for Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
9.89.8 out of 10 rating
Exceptional
(110 reviews)
Stunning Renovated Waterfront Home with Private Deepwater Dock; Windows Galore!
Southport, ME
8% off
Price is AU$8,076
AU$8,076
AU$1,154 per night
includes taxes & fees
Image gallery for Jameson Point Cottage in Scenic Friendship, Me
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Jameson Point Cottage in Scenic Friendship, Me
Friendship, ME
7% off
Price is AU$2,027
AU$2,027
AU$290 per night
includes taxes & fees
Image gallery for Step back in time to simplicity...
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Step back in time to simplicity...
Bremen, ME
8% off
Price is AU$1,605
AU$1,605
AU$229 per night
includes taxes & fees
Image gallery for Charming Home W/Harbor View: Walk to Resturants, Shops & Beach
9.49.4 out of 10 rating
Exceptional
(37 reviews)
Charming Home W/Harbor View: Walk to Resturants, Shops & Beach
New Harbor, ME
7% off
Price is AU$2,857
AU$2,857
AU$408 per night
includes taxes & fees
Image gallery for New cottage in an established vacation spot on Linekin Bay Boothbay Harbor
9.89.8 out of 10 rating
Exceptional
(12 reviews)
New cottage in an established vacation spot on Linekin Bay Boothbay Harbor
Boothbay Harbor, ME
12% off
Price is AU$2,572
AU$2,572
AU$367 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - White Head Trail
Century-old oceanfront home with wraparound porch - walk downtown, dogs OK
Sleeps 10 · 4 bedrooms · 2 bathrooms
8.88.8 out of 10
Excellentexcellent
37 reviews(37 reviews)
Boothbay Harbor Maine, Beautiful private Apartment
Sleeps 2 · 1 bedroom
9.29.2 out of 10
Wonderfulwonderful
56 reviews(56 reviews)
Unique oceanfront home with a deck, tons of natural light, & amazing views
Sleeps 4 · 2 bedrooms · 1 bathroom
8.68.6 out of 10
Excellentexcellent
56 reviews(56 reviews)
Oceanfront Cabin-Castle in Maine Woods
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Sleeps 10 · 3 bedrooms · 3+ bathrooms
8.48.4 out of 10
Very goodvery good
45 reviews(45 reviews)
Fully Remodeled Coastal Retreat with Spacious Deck and Dog-Friendly Comfort
Sleeps 10 · 5 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value