- Bailey Island
- Brunswick
- Cape Elizabeth
- Chebeague Island
- Cliff Island
- Cumberland Foreside
- Cundys Harbor
- Cushing Island
- Falmouth
- Falmouth Foreside
- Freeport
- Gray
- Great Diamond Island
- Harpswell (N,S,E&W)
- Harpswell Center
- Higgins Beach
This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Portland & Casco Bay Vacation Rentals Show this location only Back to top
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Adorable, Light-Filled Bungalow Near Beaches and Downtown - Pet Ok!
2BR/2BA
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Sleeps 4
– South Portland #973608ha
$136 - $214 per night
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Panoramic Oceanfront Views of Garrison Cove, Wills Gut and Casco Bay
5BR/3BA
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Sleeps 10
– Bailey Island #465503
$457 - $800 per night 3-7 night min stay
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Alluring Oceanfront Luxury ~ a Captivating, Maine Seaside
5BR/4.75BA
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Sleeps 8-15
– Freeport #406102
$750 - $3000 per night 3 night min stay
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Idyllic Waterfront Private Estate Located on 5-Acre Peninsula
5BR/4BA
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Sleeps 8
– Cundys Harbor #23176
$6500- $7000/wk
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Serenity at 'High View' - the Way Vacations Are Meant to Be
2BR/3BA
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Sleeps 6-8
– Harpswell (N,S,E&W) #282508
$950 - $2200/wk
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Waterfront Cottage-Private Rd,Stunning Views!
4BR+/2BA
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Sleeps 8-10
– Freeport #327966
$750- $2450
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Large House 7 Bedrooms, Close to Ocean and Sandy Beach
7BR+/4BA
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Sleeps 18
– Bailey Island #246087
$2600- $3800/wk
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Private,Charming Waterfront Estate,Indoor Pool/Spa,Outdoor Pool and Great Dock
7BR+/7BA
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Sleeps 12
– Cumberland Foreside #273539ha
$2143 per night
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Prouts Neck, Steps to the Beach
5BR/3BA
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Sleeps 10
– Prouts Neck #285420
$1500- $3000/wk
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Chanticleer Farm - Luxurious Rental in North Yarmouth, Maine
2BR+/1.5BA
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Sleeps 4-6
– North Yarmouth #262957
$1200/wk
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Chanticleer Farm - Luxurious Rental in North Yarmouth, Maine
1BR+/1BA
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Sleeps 2-3
– North Yarmouth #262969
$950/wk - $2375/mo
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Water Front 6 Bedrooms Sleeps 17 with Private Dock
6BR+/5BA
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Sleeps 2-17
– Harpswell (N,S,E&W) #378363
$700- $4500/wk
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Charming, Family-Friendly New England Style Home
3BR/1BA
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Sleeps 6-8
– Portland #455184
$175 per night 4 night min stay
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Maine Luxury Estate Nr Bowdoin,1 Mi Pvt Oceanfront! 40 Min to Portland
7BR+/7.5BA
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Sleeps 16
– Harpswell (N,S,E&W) #408934
$7000- $10000/wk
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Elegance on the Coast of Maine
5BR+/3.5BA
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Sleeps 8
– Yarmouth #402568
8500/wk
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Privacy Views and Casual Elegance_ Family Estate
5BR/4.5BA
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Sleeps 14-16
– Cundys Harbor #3543545ha
$5999 per week 7 night min stay
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Bailey Island; Waterfront House with Spectacular Sunsets
4BR/3.5BA
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Sleeps 8
– Bailey Island #358091
$2499 - $3101 per week 7 night min stay
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Private Oceanfront Retreat
4BR/2BA
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Sleeps 6
– Bailey Island #318909
$2200/wk
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Maine Island Vacation Home & Permaculture Demonstration Site
4BR+/2BA
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Sleeps 8-12
– Peaks Island #351084
$2800 - $2100
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Oceanfront Shingle Style
6BR+/4BA
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Sleeps 12-14
– Bailey Island #33280
$5500- $7500/wk
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Waterfront Vacation Home for the Whole Family, Pets Welcomed
4BR+/3.5BA
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Sleeps 8-10
– Freeport #161757
$1350- $3250/wk
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Prime Foliage Weeks Available! Privacy, Elbow Room in Coastal Maine
3BR/2.5BA
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Sleeps 6-7
– Freeport #220339
$1,295- 1,350/wk
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Custom Amenities with Wonderful Cove and Casco Bay Views
4BR+/5BA
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Sleeps 10-12
– Bailey Island #266994
$2995- $3995/wk
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Harpswell Vacation Oceanfront Rental Home
3BR/3BA
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Sleeps 8
– Harpswell Center #287481ha
$229 - $371 per night
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Private Oceanfront Paradise
3BR+/3BA
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Sleeps 6-8
– Peaks Island #341898
From $500/nt or $2,800/wk
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Waterfront, Private Dock & Cove, Fantastic Southern Views
3BR+/3BA
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Sleeps 7-9
– Harpswell (N,S,E&W) #344715
$250 - $343 per night 3-7 night min stay
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Family Friendly Home - with Nearby Water Access, Pets Welcome!
3BR/1BA
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Sleeps 5
– Harpswell (N,S,E&W) #298524
$750/wk
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On the Water! - Overlooking Freeport Harbor and Casco Bay
3BR+/2BA
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Sleeps 6-10
– Freeport #316415
Both cottages $3,000 per week + 7% tax
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Brand New Well Built Elegant Home on the Water
5BR+/3BA
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Sleeps 10-12
– Freeport #332819
1,600- $3,200/wk Dollars
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Beautiful Gardens, Private Vegetable Garden, Quiet Street.
3BR+/2BA
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Sleeps 6-8
– Bailey Island #352564
$1,200 to $9,000.00
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Heron's Rest Vacation Rental Cottage
2BR/1.5BA
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Sleeps 4
– Orrs Island #131916
$800- $1400/wk
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Beautiful, Classic Single Shingle Summer Apartment Renovated
2BR/1BA
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Sleeps 4
– Bailey Island #357971
From $1,000.00 for 2/wk $2,000.00
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Breathtaking Ocean Front Views from Every Room!
3BR/1BA
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Sleeps 5
– Harpswell (N,S,E&W) #313583
$1000- $1650/wk
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Island Cottage: Secluded by Pines, Walk to Amenities
3BR/1BA
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Sleeps 6
– Peaks Island #196828
$750- $950/wk
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'Camp Card Cove' the Way Life Should Be
4BR/3BA
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Sleeps 8-10
– Harpswell (N,S,E&W) #139207
$2450 - $2995 per week 7 night min stay
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Oceanfront Classic Beach, Kayaks, and Mooring
2BR+/1BA
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Sleeps 4-6
– Harpswell (N,S,E&W) #52692
Summer- $1500/wk
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Charming Waterfront Cabin in the Woods
2BR+/1BA
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Sleeps 4-5
– Freeport #248862
$900/wk
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5 Star Honeymoon Suite on the Ocean
Studio+/1BA
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Sleeps 2
– Harpswell (N,S,E&W) #306387
$950/wk
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Pristine Rental Across from Crescent Beach State Park
2BR+/1BA
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Sleeps 4-6
– Cape Elizabeth #24623
$1,600.00
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Portland's Old Port Close to Waterfront
1BR+/1BA
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Sleeps 2-4
– Portland #429113
$1600- $3,200/Month
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Beachfront Island Cottage with Panoramic Water Views
5BR/1BA
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Sleeps 6
– Little Diamond Island #305151
$2100 per week 7 night min stay
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May/June Specials: Beautiful Coastal Cottage with Ocean Views ~ Pet Friendly!
3BR/1BA
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Sleeps 6
– Portland #132471ha
$79 - $495 per night
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Great Summer Waterfront Cottage-Panoramic Views of Harpswell Sound
3BR+/2BA
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Sleeps 8
– Orrs Island #119460ha
$300 - $386 per night 3-7 night min stay
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1890s Oceanfront Estate with 1.5 Acre on Sandy Beach
5BR/3BA
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Sleeps 10
– Pine Point #53355
$2500- $5900/wk
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Elegant 1870 Carriage House in Exclusive West End
3BR+/2.5BA
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Sleeps 6
– Portland #241798
$350 per night 2 night min stay
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Escape to Our Peaceful Maine Island Retreat!
2BR+/1BA
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Sleeps 5
– Orrs Island #233429
$140 - $225 per night 2 night min stay
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'Schooner Landing' Cottage- Your Peaceful Respite
4BR+/2BA
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Sleeps 8
– Harpswell (N,S,E&W) #153919
$1495 - $2195 per week 7 night min stay
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Pondsea Place - Maine Island Vacation with Views of Water!
4BR+/2BA
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Sleeps 15
– Peaks Island #39583
$3,000/wk
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'Lofty' Waterfront Camp 'the Best Kept Secret in Harpswell!'
2BR+/1BA
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Sleeps 6
– Harpswell (N,S,E&W) #165589
$1050 - $1625 per week 7 night min stay
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Across from Ocean Charming,Spacious Beach House to Sandy Bch / Priv. P
4BR+/1BA
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Sleeps 7-10
– Pine Point #102586ha
$214 - $386 per night
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Woodsea Place - Maine Island Vacation in a Log Home!
4BR+/2BA
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Sleeps 16
– Peaks Island #39577
$3,000/wk
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Maine Oceanfront Home -- Year-Round Rental!
4BR+/2BA
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Sleeps 8-11
– Orrs Island #333300
From 2600/wk to 1500/wk
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Private Oceanfront Cottage - Sweeping Views
1BR+/1BA
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Sleeps 2-4
– Cape Elizabeth #55128
$1000- $1200/wk
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The Birdhouse at Willard Beach ~ a Maine Cottage at the Beach
2BR/1.5BA
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Sleeps 4-5
– South Portland #953622ha
$129 - $185 per night
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Perfect Vacation Cottage, Filled with Sunshine and Laughter.
3BR/2BA
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Sleeps 6
– Peaks Island #37511
1000 to 1700wk
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3 Bedroom Fisherman's Cottage Overlooking Mackerel Cove
3BR+/3BA
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Sleeps 6-8
– Bailey Island #86899
$1850/wk
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Charm and Convenience for Life's Wanderers
3BR/0BA
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Sleeps 6
– Kittery Point #930070ha
$250 per night 2 night min stay
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Lovely Waterfront Home W/ Deck, Dock, Sunsets! Available June, Sept, Oct.
3BR+/3BA
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Sleeps 6-8
– Freeport #236505
$2450 per week 7 night min stay
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Spectacular View at the Oceanside Retreat
3BR+/2.5BA
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Sleeps 8
– Peaks Island #123370
$500 per night 3 night min stay
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Oceanfront - Decks - Sweeping Views
3BR+/2BA
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Sleeps 6-8
– Cape Elizabeth #55087
$1800- $3000/mo
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Private Beach House Close to Portland, Maine
6BR/4.5BA
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Sleeps 10
– Cape Elizabeth #3487847ha
$3000 per week 7 night min stay
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Oceanfront Island Fantasy
4BR/1.5BA
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Sleeps 8-10
– Pole Island #83292
$2205 per week 7 night min stay
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Woodland Paradise, Shingle Home on Private Tidal Ocean Front
3BR+/2.5BA
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Sleeps 6-8
– Brunswick #352583
From $1700.00 per week
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Sunny, 1835 Brownstone, Downtown, Portland Condo
1BR+/1BA
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Sleeps 4
– Portland #287840
From $185.00; call for long term rates
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New as of June 2012 - Ocean Breeze Cottage on Casco Bay with Beach
2BR+/1BA
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Sleeps 6
– Bailey Island #419998
$50 - $330 per night
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Peaceful and Secluded Oceanfront Post & Beam Home on Casco Bay
2BR+/1.5BA
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Sleeps 6
– Freeport #141221
$225 - $283 per night 2-7 night min stay
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Attractive Oceanfront Home W/ Spectacular Gardens, Brunswick,Me
3BR+/2.5BA
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Sleeps 8
– Brunswick #58799
$2000-$2200/wk - $6500/mo
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Waterfront Estate Guest Cottage W/Private Beach Near Portland
4BR/2BA
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Sleeps 8
– Cumberland Foreside #177262
$1400- $2200/wk
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Maine Island Cottage, Lower Goose Island
3BR+/1BA
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Sleeps 8
– Lower Goose Island #343952
$1500/wk
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Cagasa Cottage: Oceanview, Handicap Friendly, on Seashore Ave
3BR+/2BA
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Sleeps 7-10
– Peaks Island #355415
$900 to $1500/week $U.S.
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Breath-Taking Waterfront Cottage with Boat Dock
1BR+/1BA
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Sleeps 0-4
– Peaks Island #344620
Weekly off season rates Starting @ $1600
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Amazing Sunsets from Waterfront Cottage - Peaceful, Cozy
1BR+/1BA
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Sleeps 2-4
– Harpswell (N,S,E&W) #173012
$750- $1000/wk
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Spectacular Oceanfront House on Maine Coast
6BR/2BA
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Sleeps 10
– Orrs Island #294757
$3250 - $3750/wk
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Seaside Cottage
2BR+/1BA
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Sleeps 4-6
– Freeport #303479
From $1000- $1250/wk
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Waterfront Home with Fantastic Bay and Sunset Views
4BR/2BA
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Sleeps 9
– Bailey Island #365995
$2200-$2900/wk - see rate detail
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Charming Cottage at Exclusive Higgins Beach in Scarborough
4BR/2.5BA
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Sleeps 8
– Higgins Beach #128537
$1300- $3000/wk
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Oceanfront Peaceful Cottage, Spectacular View, Private Beach
3BR+/2.5BA
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Sleeps 6-8
– Orrs Island #396368
From $1200/wk
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Charming 3 Bedrm Island Cottage, Near Playground, Pet Friendly
3BR/1BA
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Sleeps 7
– Peaks Island #341799
$1250/wk
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Architectural Lighthouse
6BR+/3BA
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Sleeps 13-15
– Orrs Island #331962
$900/wknd - $2600/wk
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Beautiful Waterviews- Potts Point - June Value Weeks- Save 30%*
3BR+/2BA
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Sleeps 6
– Harpswell (N,S,E&W) #345817
$1400- 2000/wk
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Romantic Maine Family Cottage Near Sandy Beach
3BR/1BA
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Sleeps 4-6
– South Portland #466164
$150 - $200 per night 2 night min stay
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Great Ocean View Summer Cottage Rental on Great Diamond Island
4BR/1BA
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Sleeps 7-9
– Great Diamond Island #368955
$1500/wk
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Newly Converted Seaside Post & Beam 1886 Barn. Luxury & Views
3BR+/2BA
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Sleeps 10
– Harpswell Center #373960
$1500 - $3600/wk
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Maine Cottage on Water in Brunswick
2BR/1BA
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Sleeps 6
– Brunswick #187940
$150 per night 5 night min stay
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Steps from
Willard Beach with Ocean Views.
1BR/1BA
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Sleeps 2
– South Portland #12490
$125 - $157 per night 4-7 night min stay
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Tidal Cove- Informal Charming Cottage Rebuilt to Passive Cozy
2BR/1.5BA
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Sleeps 4
– Harpswell (N,S,E&W) #59715
$175 per night 3 night min stay
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Sunset Cove Cottage - Right on the Water - Big Yard - Peaceful
3BR/2BA
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Sleeps 6
– Harpswell (N,S,E&W) #11932
$900- $1650/wk
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Cundy's Harbor Oceanfront House - Private, Peaceful, Beautiful, & Convenient
3BR/2BA
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Sleeps 6-8
– Harpswell (N,S,E&W) #286712ha
$150 - $229 per night 3-7 night min stay
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Deck at Ocean's Edge, Lobster Boats, Birds, Quiet, Peaceful
1BR+/1BA
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Sleeps 4
– Cundys Harbor #24127
$700- $995/wk
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Oceanfront on the Rocks, Lobster Boats, Seabird
1BR/1BA
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Sleeps 2
– Cundys Harbor #24126
$595- $825/wk
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Spacious Water Front Property - 5 Bedrooms, 3 +1/2 Baths
5BR+/3.5BA
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Sleeps 10-12
– Freeport #81855
$450 - $525 per night 3-7 night min stay
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Spectacular Farm House with Ocean View of Crescent Beach
6BR/3BA
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Sleeps 8
– Cape Elizabeth #84057
$3500 per week
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Oceanfront Cottage, Kayaking, Lobster Boats, Relax, Seabirds
3BR/1BA
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Sleeps 6
– Cundys Harbor #24124
$900- $1495/wk
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Lovely Ocean-Front Guest Suite on 10-Acre Charming Private Peninsula
1BR+/1BA
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Sleeps 4-5
– Brunswick #93644
$1,145 /4 NIGHTS OR $1,700/ WEEK
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Cozy Island Hideaway
2BR+/1.5BA
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Sleeps 4-5
– Peaks Island #118778
$110 - $245 per night 2-7 night min stay
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Pine Point Beach House - Steps to Beach
3BR+/1BA
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Sleeps 6-8
– Scarborough #224452
$1000- $1650/wk
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Short Walk to Crescent Beach/Private Rd/Beautiful View -Dates Still Available!! 3BR/1.5BA – Sleeps 6 – Cape Elizabeth #348787
Special offer Save $675.00 per week June 8 - 22
Jun 8, 2013 to Jun 22, 2013
$1050 - $1925 per week 7 night min stay -
Cottage Aerie with Expansive Views of Lowells Cove
2BR/1BA
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Sleeps 4
– Orrs Island #282172
$100 - $136 per night
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Lake View Home on Little Sebago
3BR+/2BA
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Sleeps 6-8
– Gray #178343
$150 - $200 per night 2 night min stay
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Beautiful Victorian Cottage Fantastic Oceanview in Cape Elizabeth, Me
3BR/1.5BA
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Sleeps 6
– Cape Elizabeth #964385ha
$1150 - $1450 per week 7 night min stay
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Adorable, Light-Filled Bungalow Near Beaches and Downtown - Pet Ok!
2BR/2BA
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Sleeps 4
– South Portland #973608ha
Overview of Portland & Casco Bay Vacation Rentals
Portland Vacation Rentals for a Year-Round Tourist Destination
As a year-round tourist location, it’s hard to beat Portland and Casco Bay in Maine. Portland vacation rentals are ideally placed for this culturally and historically rich area. Day and night, the bustling Portland harbor is buzzing with activity, with tourist boats coming and going, fishermen at work and restaurants filled with people. Choose a Casco Bay lodging choice near the harbor to be in the middle of the action. You will find a Maine lodging choice to suit any family or group of friends looking for a vacation in this scenic area.
Portland Vacation Rentals in the Largest of Maine’s Cities
Portland is the largest of Maine’s cities and it is the hub of its renowned art community. Thus, Portland vacation rentals are in one of the most sought-after locations in the region. Dating from the 1800s, the Old Port is now a high-class shopping area with a wide variety of restaurants around your Casco Bay lodging choice. The city takes its heritage seriously and buildings around your Maine lodging choice are maintained to an exceptionally high standard.
Casco Bay Lodging for Ferries and Hot Air Balloons
A benefit to Portland vacation rentals is their proximity to the ferries to Nova Scotia. It’s worth jumping a ferry to head off to Casco Bay’s Calendar Islands for a great day out. The adventurous traveler in a Casco Bay lodging choice might prefer to undertake a slightly more unusual mode of travel and opt for a hot air balloon trip as a novel way to see the region. Staying in Maine lodging, you will wonder how many times you will have to return before you’ve seen it all!
Maine Lodging For Culture for Kids
For the culturally minded, there are so many museums and so much history here that you will struggle to fit it all in within just one vacation. Portland vacation rentals cater for the culturally minded children too with their own museum. From Casco Bay lodging you will find an amazing variety of walks and excursions to be undertaken. While staying in a Maine lodging, there is also the chance to see the Portland Pirates play hockey or the Sea Dogs if baseball is your game.