Holiday houses in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Apartment in Portland

4.82 out of 5 average rating, 354 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!

18–25 Feb

$142 NZD per night

Superhost

Apartment in Portland

4.87 out of 5 average rating, 383 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!

3–10 Nov

$253 NZD per night

Guest favourite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! It has heat, A/C, and fans. Bonus: 2 friendly dogs and a cat that will be around the property during your stay. STHR-000718-2018

8–15 Sep

$285 NZD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 114 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!

25 Oct – 1 Nov

$193 NZD per night

Guest favourite

Guest suite in Scarborough

4.98 out of 5 average rating, 139 reviews

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

10–17 Apr

$242 NZD per night

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.

28 Oct – 4 Nov

$279 NZD per night

Superhost

Apartment in Portland

4.78 out of 5 average rating, 307 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

26 Apr – 3 May

$223 NZD per night

Guest favourite

Apartment in Portland

4.93 out of 5 average rating, 560 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

9–16 Jan

$190 NZD per night

Guest favourite

Apartment in Scarborough

4.8 out of 5 average rating, 406 reviews

Quaint, clean, convenient - peaceful in Pine Point

Welcome to your own private beach nest! A cozy, clean, beach retreat with a cottage feel! You have all of the essentials to eat, sleep, beach and explore the great coast of Maine. Plenty to do and see here at the heart of Morgan's Corners a mere 500 feet from Pine Point beach. Spend your time relaxing and rejuvenating in our cozy place! Bird watch in the marsh sanctuary, enjoy lobsters on the dock or soak up the sun on beautiful Pine Point beach!

9–16 May

$185 NZD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 174 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.

30 Oct – 6 Nov

$263 NZD per night

Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 199 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!

26 Dec – 2 Jan

$202 NZD per night

Guest favourite

Guesthouse in Windham

5.0 out of 5 average rating, 219 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.

28 May – 4 Jun

$245 NZD per night