Greater Portland Vacation Rentals & Cabin Rentals - 19 Rentals Available

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1 / 16

Peaks Island Home
3 BR / 2.5 BA / Sleeps 8 3 8 6 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2.5 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This was our second time staying at Oceanside Retreat, and we felt that we were returning to see an old friend. The photos and descriptions cannot possibly do justice to the spectacular setting and overall feel of the house. Although the house is not..."
- Melissa Kessler Ingersoll, Devon,PA
(5) Excellent (5 reviews)
1 / 20

Scarborough Villa
10 BR / 5.5 BA / Sleeps 24 10 24 Min stay varies
Villa / 10 Bedrooms / Sleeps 24
10 bedrooms 5.5 bathrooms Sleeps 24
High Speed Internet • Dishwasher • Microwave
"Wow - what a great place for a family reunion - very large group of people and we never felt crowded because we were spread out over three levels. House offers everything - large open gathering spaces with decks and amazing views, gourmet kitchen,..."
- sue, Western Massachusetts
(7) Excellent (7 reviews)
1 / 13

Portland Condo
2 BR / 2 BA / Sleeps 4 2 4 7 night min stay
Condo / 2 Bedrooms / Sleeps 4
2 bedrooms 2 bathrooms Sleeps 4
High Speed Internet • Dishwasher • Microwave
"Beautifully furnished and ideally located for walking the city of Portland or sitting and enjoying a serene view of Casco Bay. Restaurants, markets and touring opportunities are minutes away and very accessible by walking or biking. The complex owner..."
- Maureen Lewis, Naples, Florida
(5) Excellent (5 reviews)
1 / 8

Freeport Cottage
3 BR / 2 BA / Sleeps 10 3 10 2 night min stay
Cottage / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"Hands down the cutest nicest little place to stay! Excellent accomdations, quaint town. Loved it and will be booking again in the near future!"
- Annie Minske, Minnesota
(6) Excellent (6 reviews)
1 / 12

Cape Elizabeth Cottage
1 BR / 1 BA / Sleeps 4 1 4 7 night min stay
Cottage / 1 Bedroom / Sleeps 4
1 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Microwave • DVD Player
"The cottage was cute and comfortable, perfect for 2 people. The bed was great and the living room allowed us to relax with a beautiful view of the ocean. The neighbors were a bit close but we still felt great about the location. Only bad thing was the..."
- Lori Foote, Windsor, CT
(2) Excellent (2 reviews)
1 / 13

Scarborough Home
4 BR / 2.5 BA / Sleeps 6 4 6 Min stay varies
Home / 4 Bedrooms / Sleeps 6
4 bedrooms 2.5 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"My family had the best time in Maine and Jen's house was the perfect landing spot. We took advantage of all of the area attractions and loved going back to this beautiful home. Jen was extremely helpful and made us feel like family. Would recommend..."
- Cap Wolfe, South Yarmouth, MA
(4) Excellent (4 reviews)
1 / 12

Freeport Home
5 BR / 4.5 BA / Sleeps 15 5 15 3 night min stay
Home / 5 Bedrooms / Sleeps 15
5 bedrooms 4.5 bathrooms Sleeps 15
High Speed Internet • Dishwasher • Microwave
"We rented this beautiful home for eight nights for my sons wedding When we arrived the house smelled of garbage and was untidy I contacted Jeff and he fixed the problem after two days We reached an agreement and I was refunded for my troubles Otherwise..."
- Jeanne Travis, Scituate ma
(1) Excellent (1 review)
1 / 29

South Portland Home
3 BR / 2 BA / Sleeps 10 3 10 3 night min stay
Home / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
"This is the third year that we have stayed at this property. Our family comes from 3 states and 3 continents to stay here and the house accommodated all 10 of us comfortably. The owner is easy to work with. When the electronic lock quit working on the..."
- Ed Baxter, Missouri
(11) Excellent (11 reviews)
1 / 24

Scarborough Home
5 BR / 4 BA / Sleeps 12 5 12 Min stay varies
Home / 5 Bedrooms / Sleeps 12
5 bedrooms 4 bathrooms Sleeps 12
High Speed Internet • Dishwasher • Microwave
"Spent the weekend at the unit closest to the water with 4 other couples and had a great time. The accomodations were awesome and the location was great. The pictures and the description are spot on. Everything was there that we needed."
- deborah munkittrick, Peacham VT
(2) Excellent (2 reviews)
1 / 30

Scarborough Home
6 BR / 3 BA / Sleeps 16 6 16 Min stay varies
Home / 6 Bedrooms / Sleeps 16
6 bedrooms 3 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
"A beautiful home for our family to come together and enjoy Maine. This house had everything. We sat on the porch with our morning coffee and enjoyed the marsh birds. Swam in the ocean. Enjoyed a family lobster dinner and watched the Olympics together ..."
- Erin Carrington, Oregon
(1) Excellent (1 review)
1 / 23

Windham Cabin
2 BR / 1 BA / Sleeps 5 2 5 Min stay varies
Cabin / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
Microwave • Gas Grill • Parking Included
"We are a family of four (2 of whom are teenage girls). At first they were skeptical about the prospect of no TV or wifi - but that went away within our first hours on the water. Paddle boards, kayaks, canoes, rope swings, and great swimming kept ..."
- Susan Marble Cuthbert, Braintree, MA
(8) Excellent (8 reviews)
1 / 15

Cape Elizabeth Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
"This home is remarkable- it is fully updated with gorgeous furnishing, and has so many items for cleaning, toilet paper etc. that I have not found with rentals. The view to the ocean is amazing, and there are even binoculars to look at the boats..."
- Deborah Rosenfeld Kohls, Chapel Hill, NC
(7) Excellent (7 reviews)
1 / 25

Scarborough Home
5 BR / 3 BA / Sleeps 14 5 14 Min stay varies
Home / 5 Bedrooms / Sleeps 14
5 bedrooms 3 bathrooms Sleeps 14
High Speed Internet • Dishwasher • Microwave
"We stayed at this house third week in August and it was great. The house is very well kept and has a nice deck and fenced in yard. House was filled with nice glasses and dishes and very comfy beds. Beach is a two minute walk away."
- michelle oconnor, Framingham,ma
(7) Excellent (7 reviews)
1 / 8

Orr's Island Apartment - 14.5 mi away
2 BR / 1 BA / Sleeps 6 2 6 Min stay varies
Apartment / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"My vacations are usually full of activity. I am not a beach or resort person but at this time, I really just needed a comfy spot to relax and have 'no agenda'. The cottage was so clean and stylish. The view was amazing and you felt like a local just ..."
- Patti Blake, New Brunswick, Canada
(3) Excellent (3 reviews)
1 / 54

Sebago Lake Cottage - 14.5 mi away
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We have been coming here for several years with our granddaughters and never tire of this lovely spot. The cottage is always immaculate, well stocked, and you can count on a pie to be waiting for you in the refrigerator. The owners, Bob and Marian,..."
- Christine Maloney-Littlefield, North Hampton, N.H.
(2) Excellent (2 reviews)
1 / 8

Old Orchard Beach Villa - 15.6 mi away
7 BR / 5 BA / Sleeps 18 7 18 7 night min stay
Villa / 7 Bedrooms / Sleeps 18
7 bedrooms 5 bathrooms Sleeps 18
High Speed Internet • Dishwasher • Microwave
"Beautiful views from the house and just a few steps to the beach. Lots of privacy and space to spread out on the beach (the crowds seemed to stick closer to public parking lots/bathrooms). The house has tons of space for kids and adults to relax in separate..."
- Suzanne Deshaies, New Hampshire
(1) Excellent (1 review)
1 / 12

Raymond Cabin - 15.6 mi away
5 BR / 2 BA / Sleeps 10 5 10 7 night min stay
Cabin / 5 Bedrooms / Sleeps 10
5 bedrooms 2 bathrooms Sleeps 10
Microwave • TV (Antenna) • DVD Player
"We just got back from our vacation on Panther Pond, Raymond Maine, and had a great time. The waterfront is perfect, pretty deep off the dock for diving and also a great sandy access with stairs, the beat of both worlds! We rented a boat for the..."
- Melody Landry, Connecticut
(2) Excellent (2 reviews)
1 / 8

Raymond Cottage - 15.6 mi away
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Microwave • TV (Antenna)
"This rental was amazing and so much more than I could have hoped for. The owners were fantastic and accomodating. The view and peaceful quiet was relaxing."
- Christine Doyle, Lewiston, Maine
(4) Excellent (4 reviews)
1 / 11

Raymond Cottage - 15.8 mi away
2 BR / 1 BA / Sleeps 6 2 6 7 night min stay
Cottage / 2 Bedrooms / Sleeps 6
2 bedrooms 1 bathroom Sleeps 6
High Speed Internet • Microwave • Air Conditioning
"Amy was wonderful to work with. I emailed multiple people and Amy was very quick to respond. Coordinating our arrival was easier than I thought it would be and could not have gone any smoother. I hadn't even been to the cottage yet and was super impressed...."
- Tammy Ricci, South Portland, Maine
(3) Excellent (3 reviews)
1 / 6

Brunswick Home - 15.8 mi away
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
"We have stayed in many places in Maine over the years, and this is one of our favorites. Far enough from town to be very peaceful, but close enough to run to the store or have dinner out, the location was perfect. Every morning we had coffee on the..."
- Kelly Rowe, Flagstaff, AZ
(6) Excellent (6 reviews)
1 / 11

Old Orchard Beach Apartment - 16.0 mi away
2 BR / 1 BA / Sleeps 4 2 4 Min stay varies
Apartment / 2 Bedrooms / Sleeps 4
2 bedrooms 1 bathroom Sleeps 4
High Speed Internet • Dishwasher • Microwave
"The place is perfect in every way. The descriptions are exactly what the bungalow offers. Clean, bright and nicer than home away from home. Bob and Anita are a pleasure to meet, but the place is yours to enjoy. We cannot wait to get back again."
- John Gerken, New Hampshire
(27) Excellent (27 reviews)
1 / 6

Old Orchard Beach Home - 16.2 mi away
6 BR / 3 BA / Sleeps 23 6 23 7 night min stay
Home / 6 Bedrooms / Sleeps 23
6 bedrooms 3 bathrooms Sleeps 23
High Speed Internet • Microwave • Air Conditioning
"We lost our Dad in June of 2016 and had planned on taking him to Maine with us in July. So it was with heavy hearts we left for our trip. But the house was wonderful...plenty of room for everyone and right on the water. We found ourselves sharing stories..."
- Sharon Reichert, Roseville, California
(1) Excellent (1 review)
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About Greater Portland

Charming cobblestone streets, lighthouses, cultural events, and outdoor activities are just a few of the highlights families will discover in Maine’s largest city: Portland. The city has been home to writer Stephen King, actress Liv Tyler and poet Henry Wadsworth Longfellow, and visitors are certain to understand why notable people have been drawn to Portland over the years. Enjoy a level of privacy simply unheard of in hotels by booking one of the many Portland vacation rentals and explore the plethora of adventures this coastal city has to offer.  

Climate

Portland attracts visitors year-round as a result of its snow-covered peaks perfect for skiing in the winter and its gorgeous beaches that are home to summer fun. Winter lows can dip below 0 degrees Fahrenheit while summer temperatures generally stay in the 70s. Portland’s high season runs from mid-June until October, when many come to revel in the colorful fall foliage. Bring layers when visiting this destination as New England weather is oftentimes unpredictable and can vary significantly throughout the year. 

Neighborhoods

As Maine’s largest city, Portland is home to many neighborhoods and districts where hubs of cultural activities are located. Those considering Portland vacation rentals will find lots of options within neighborhoods, including: Back Cove, Deering Center, Downtown District, West End, Hobart Street, India Street, Valley Street, Stroudwater, Nasons Corner, Parkside and Rosemont. Additionally, the Arts District is located within the West End and Bayside, the Waterfront district is on the coast, and the Old Port district is nestled between the Arts District, the neighboring Government district and the Waterfront region. Portland’s Downtown District booms with activity, and visitors will find attractions, art walks, and events that take place here on a daily basis.

Things to Do

Situated approximately 100 miles north of Boston, Massachusetts, Portland sits on Casco Bay and offers lots of opportunities for water-based recreation, exploring majestic seaside landscapes and seeing some of the best tourist attractions in New England. Boat charters and cruises are available and offer everything from whale-watching tours to an exploration of one of Casco Bay’s islands. Visit the Portland Head Light, which dates back to 1971, or take a scenic ferry ride with Casco Bay Lines to see the variety of lighthouses scattered along the coast or head out with Lucky Catch Cruises to spend a day in the life of a Maine Lobsterman. Bask in the outdoors at East End Beach and frolic in the waves during the summer.

When you aren’t marveling at the abundance of opportunities to revel in the Atlantic Ocean, you’ll find plenty to do in one of Portland’s many districts. Take a trip to East Royce Mountain to enjoy the variety of hiking trails in the area. The Portland Museum of Art and Portland Children’s Museum and Theater of Maine ensure that there are always cultural and educational activities on the itinerary. Historic sites of interest like the Victoria Mansion and the Wadsworth-Longfellow House provide a glimpse into early life in Maine. Children who are fascinated with subjects like Bigfoot or the Loch Ness Monster will love the International Cryptozoology Museum. It is more of a collection than a museum and die-hard fans of strange and bizarre animals will find this one stop that can’t be missed. 

Food & Dining

Portland has made a name for itself as a fantastic destination for foodies. Many of the city’s best dining establishments can be found in Portland’s downtown, including the Arts District and the Old Port area. Here, you’ll find lobsters freshly hauled in from the Gulf of Maine, locally brewed beers, and award-winning dishes at a variety of restaurants. Street and Co. has an abundance of seafood on the menu and Eventide Oyster Company offers reasonably-priced small plates, so you can sample a variety of seafood. Allagash Brewery and Shipyard Brewing Company offer tours and tastings for the 21+ crowds to enjoy.

Events

The visiting family will find numerous activities suitable for all ages, including some of Maine’s most notable culinary delights and seafood festivals. Live music, art and historical events abound in this charming city. Annual lobster fests and clambakes are popular events that draw huge crowds. Every June, the Old Port Festival kicks off the summer with local food and drinks, multiple stages of music and Maine-made arts and crafts. The fall months bring Harvest on the Harbor, Maine’s premier food and wine festival held in October and Maine Brewers Festival the following month. In December, Portland hosts the Phyzkids Festival that focuses on magicians, vaudeville, and entertainment acts children will enjoy. 

With a bustling arts district, beaches, museums, and spectacular scenic views, Portland offers adventure and excitement the entire family will enjoy on vacation. By choosing Portland vacation rentals, you can make certain you have all the luxuries of living in a home while enjoying your time in this beautiful, historic city.