Holiday houses in Portland

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Top-rated holiday rentals in Portland

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Superhost

Apartment in Portland

4.82 out of 5 average rating, 351 reviews

Spacious and Comfortable Private Apartment

Third floor (i.e. a few stairs) spacious apartment with a private entrance. Walking distance to Thompson’s Point, Maine Med and many other trails and attractions. The Old Port is a 5 minute drive (1.5 mi.). There is plenty of free street parking available. Space heaters warm the space in the winter, and a/c is provided in the summer. The house is shared by first floor tenants while our family occupies the second floor. Again, several stairs to navigate, but quite comfortable once you settle in!

20 – 27 Nov

$1,307 AUD total

Superhost

Apartment in Portland

4.88 out of 5 average rating, 377 reviews

Modern East End studio, perfect Portland home base

Enjoy all that Portland has to offer from this clean, modern, and spacious studio in the city's hippest neighborhood. Walk one block to enjoy Duckfat frites at the Oxbow beer garden or head down Washington Ave to sample the best restaurants in Portland including Drifter's Wife, Cong Tu Bot, and Izakaya Minato, among others. Walk 5 mins up Munjoy Hill to picnic on the Eastern Promenade overlooking Casco Bay or 10 mins down into the Old Port. Do it all from this beautiful and private apartment!

11 – 18 Nov

$1,636 AUD total

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 111 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

12 – 19 Sept

$1,474 AUD total

Superhost

Apartment in Portland

4.82 out of 5 average rating, 426 reviews

Walk-able Portland Studio

NEWLY RENOVATED! Cozy studio apartment in a historic building, located in Portland's East End Neighborhood. This location can't be beat! The Space features original hardwood floors, and large windows, subway tiled shower and thoughtful decor. Portland Food Co-Op is directly next door, as is the Walgreen's. Walking distance to Eventide, Honey Paw, Duck Fat, Hugos, Little Woodfords, LB Kitchen, Washington Ave Breweries and Distilleries and Old Port shopping district.

29 Oct – 5 Nov

$1,940 AUD total

Superhost

Apartment in Portland

4.78 out of 5 average rating, 303 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

5 – 12 Sept

$1,409 AUD total

Superhost

Apartment in Portland

4.79 out of 5 average rating, 433 reviews

The Munjoy Hill Experience

Enjoy Portland's East End like a local with this stunning open-concept apartment as your home base! Located in the heart of Portland, you're just a walk away from the Eastern Promenade, brunch at a local favorite-The Front Room, Portland's lively night life, and so much more. The apartment easily fits two guests and features a queen bed, a mini kitchen, a family room with a tv and a bathroom. Ideal for traveling professionals, and vacationists alike.

26 Apr – 3 May

$1,493 AUD total

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 169 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

24 Nov – 1 Dec

$1,629 AUD total

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 196 reviews

Gorgeous Studio 2 Blocks from Eastern Prom!

Located in Portland's trendy East End and within walking distance to the Old Port and Downtown, this beautiful studio is only 2 blocks from the Eastern Promenade and Casco Bay! You will have the Unit entirely to yourself with its own entrance, air conditioning, kitchenette, queen sized bed and an additional pull out single. Easily walk to all of the cool breweries, great restaurants, coffee shops, and night life! Welcome to Portland!

3 – 10 Nov

$1,310 AUD total

Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 217 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

10 – 17 July

$1,588 AUD total

Guest favourite

Guest suite in Freeport

4.95 out of 5 average rating, 195 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.

18 – 25 May

$870 AUD total

Guest favourite

Apartment in Portland

4.96 out of 5 average rating, 151 reviews

Compact & Complete in residential neighborhood

Completely renovated ground level apartment in Deering section of Portland. Walk to off-peninsula restaurants, coffee and wine shops. Nearby trails for walking or biking. Near UNE's Portland Campus. On bus line to easily reach downtown Old Port area, USM and other attractions. Off street parking for your car. Portland STHR-0010302019

16 – 23 Nov

$1,741 AUD total

Guest favourite

Home in Lisbon

4.94 out of 5 average rating, 331 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Chill on the porch after exploring a scenic local walking trail and soak up the serenity of this breezy blue and white hideaway. Striped oars, starfish, smooth shells, and ocean scenes blend with shades of teal and aqua for a thoroughly calm space. There are EV chargers behind the post office. It’s around a block and a half.

21 – 28 Jan

$863 AUD total