Holiday Homes in Portland

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Portland and around

Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is €200
includes taxes & fees
20 Aug - 21 Aug
Charming Studio apartment with WiFi, AC in welcoming Portland
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (2)
"This apartment is great- the furnishings are cute and the bed is comfy. It has a kitchen with all of the cookware I needed, and off-street parking is awesome. I liked that it was really convenient to downtown, but outside of the busy, touristy parts of town. The owners were communicative, but not intrusive. It was overall a great experience. I would definitely stay here again."
The price is €179
includes taxes & fees
17 Aug - 18 Aug
Private Entrance Residential Portland
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Property grounds

1200 sq ft ♦ West End Townhouse ♦ Perfect Location

8.6 out of 10, Excellent, (56)
"Quiet neighborhood. Nice place"
The price is €244
includes taxes & fees
8 Sept - 9 Sept
1200 sq ft ♦ West End Townhouse ♦ Perfect Location
Willard Beach–Private Apt Near Portland & Parks
Interior

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is €230
includes taxes & fees
15 Sept - 16 Sept
Willard Beach–Private Apt Near Portland & Parks
Elegant condo - walk to Portland's best restaurants & Old Port
Fridge, microwave, oven, stovetop

Elegant condo - walk to Portland's best restaurants & Old Port

9.4 out of 10, Exceptional, (62)
"Right off a Main Street with tons of food and drink options. Loved the area, felt safe and fun. Close to walking trails as well. Inside decor was nice. "
The price is €375
includes taxes & fees
17 Aug - 18 Aug
Elegant condo - walk to Portland's best restaurants & Old Port
Sauna & fire table near Portland's Back Cove
Terrace/patio

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is €328
includes taxes & fees
21 Aug - 22 Aug
Sauna & fire table near Portland's Back Cove
Mint Ocean Promenade Condo, Steps to Old Port
Private kitchen

Mint Ocean Promenade Condo, Steps to Old Port

10.0 out of 10, Exceptional, (1)
The price is €308
includes taxes & fees
2 Sept - 3 Sept
Mint Ocean Promenade Condo, Steps to Old Port
Walkable near downtown 1 Bedroom
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Walkable near downtown 1 Bedroom

The price is €179
includes taxes & fees
10 Sept - 11 Sept
Walkable near downtown 1 Bedroom
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (2)
"GoodLocation, very clean. Would stay again "
The price is €483
includes taxes & fees
9 Sept - 10 Sept
Luxury on Back Cove - Three Gables
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

6.0 out of 10, (1)
"Before check in the host was kind and incredibly communicative. Upon check out they asked how our stay was and I wrote them a message saying I’d rather discuss this before leaving a bad review but they left me on read… When we arrived there were so many unhoused folx outside the apt we didn’t feel safe entering. we literally saw a woman being chased/harassed while we were pulling up. If I wasn’t with my partner I would’ve had to cancel due to feeling unsafe. I have no bad feelings about unhoused...
The price is €183
includes taxes & fees
24 Aug - 25 Aug
Studio Unit Walkable Everywhere
Willard Square Family Home
Property grounds

Willard Square Family Home

9.6 out of 10, Exceptional, (7)
"A funky place. Liked the decor. "
The price is €742
includes taxes & fees
17 Aug - 18 Aug
Willard Square Family Home
Spacious Portland Home + Parking
Private kitchen

Spacious Portland Home + Parking

Spacious Portland Home + Parking
Spacious and Centrally Located! Two Connected Apartments- Sleeps 12
Private kitchen

Spacious and Centrally Located! Two Connected Apartments- Sleeps 12

Spacious and Centrally Located! Two Connected Apartments- Sleeps 12
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Outdoor spa tub

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Spacious 7-bedroom house in marvelous Portland with AC, WiFi
Interior

Spacious 7-bedroom house in marvelous Portland with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
"Great, renovated set of three units. The location was convenient along with the three parking spots. Window and mini split AC units worked well. The loft space and roof deck on the third floor was particularly nice for hanging out. The ice makers didn’t work and a couple other maintenance issues, but the owner said they would be fixing them. All in, a great space for our family of 11 to explore Portland. "
The price is €1,370
includes taxes & fees
17 Aug - 18 Aug
Spacious 7-bedroom house in marvelous Portland with AC, WiFi
Modern & Sunny House Steps from the Promenade. Private Parking!
Terrace/patio

Modern & Sunny House Steps from the Promenade. Private Parking!

10.0 out of 10, Exceptional, (29)
"Perfect stay for a quick trip to Portland! "
The price is €532
includes taxes & fees
10 Sept - 11 Sept
Modern & Sunny House Steps from the Promenade. Private Parking!
Luxury King Room with Parlor and Balcony
Property grounds

Luxury King Room with Parlor and Balcony

The price is €615
includes taxes & fees
7 Sept - 8 Sept
Luxury King Room with Parlor and Balcony
Beautiful West End Apartment
Interior

Beautiful West End Apartment

The price is €398
includes taxes & fees
2 Sept - 3 Sept
Beautiful West End Apartment
Modern Getaway by the Sea
Fridge, microwave, oven, stovetop

Modern Getaway by the Sea

The price is €506
includes taxes & fees
14 Sept - 15 Sept
Modern Getaway by the Sea
Historic Elegance in the Heart of Portland
Dining

Historic Elegance in the Heart of Portland

10.0 out of 10, Exceptional, (2)
"Used the space for our bridal party for the weekend as well as hosting our rehearsal dinner (35ppl). Staff/owners are very attentive and helpful- Gave us exactly what we wanted for our dinner and more. Guests all commented on the house/backyard and how beautiful the setup looked for the party. We would highly recommend this space for an event or just a stay with friends. "
The price is €1,855
includes taxes & fees
19 Aug - 20 Aug
Historic Elegance in the Heart of Portland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Portland Hotel Reviews

Inn at St John Portland In-Town

Inn at St John Portland In-Town

10/10 Excellent
"I opted for the economy of the shared bath. It saved me a lot of money. I can't offer an opinion about the rooms with private baths. My room was very good. I will stay here again."
James 1-night trip
Posted 7 hours ago
Inn at St John Portland In-Town