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Holiday Homes in Portland

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in Portland

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (13)
"I had such a good time here that I actually added three more weeks so this is the first of three reviews as I booked them separately. The host was really nice working with me and the associate that supports any household requests as well. Everything works perfectly, but the host associate was nice to come and anticipate the batteries on the smart lock would be running low and came and changed them along with leaving me extra snow melt, and a shovel after clearing the walkways. The house is well...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Amazing Lakefront Property
Dining

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property
NEW-Another Fun Downtown Location 1st floor
Interior

NEW-Another Fun Downtown Location 1st floor

2.0 star property
10.0 out of 10, Exceptional, (9)
"It was a nice quiet valuable time spent together .just what we needed for that very special memorable time. Thanks."
NEW-Another Fun Downtown Location 1st floor
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is AU$1,345
includes taxes & fees
3 Mar - 4 Mar
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Island Vibes Home
Interior

Island Vibes Home

9.8 out of 10, Exceptional, (13)
"House was just as described. Clean and well stocked. Communication and instructions were clear. Great location. "
Island Vibes Home
NEW 5Bed Close to Bloomfield Center & Golf Courses
Interior

NEW 5Bed Close to Bloomfield Center & Golf Courses

2.0 star property
10.0 out of 10, Exceptional, (2)
"Omg i dont even know where to start but this property was phenomenal love it i would recommend a million times are more all im ask since this a newly released property plz take care of it like i did so otheres can have our experience clean after ur self if u can but quite spacious parking great nth to worry about 3 to 5 mins from most convenient places "
The price is AU$1,049
includes taxes & fees
3 Mar - 4 Mar
NEW 5Bed Close to Bloomfield Center & Golf Courses
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (2)
"We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming. "
The price is AU$324
includes taxes & fees
23 Feb - 24 Feb
Family Stays: Middletown, CT
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Fridge, microwave, oven, stovetop

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice clean 3 bedroom that was as described. It was a short drive to downtown West Hartford."
The price is AU$472
includes taxes & fees
3 Mar - 4 Mar
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is AU$541
includes taxes & fees
20 Feb - 21 Feb
Blue Back Bungalow
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos
Outdoor pool

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos
Storybook Cottage
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Storybook Cottage

10.0 out of 10, Exceptional, (1)
"Very charming property, accurate description per listing. Very clean and overall a great stay."
Storybook Cottage
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Fridge, microwave, oven, stovetop

A “Wow” Experience everywhere there is something to stimulate your mind Interest

9.4 out of 10, Exceptional, (3)
"Tasteful decor. Very clean. Not too far from the city. Quiet, safe neighborhood. Host was very friendly and super responsive! Would definitely recommend!"
A “Wow” Experience everywhere there is something to stimulate your mind Interest
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Fridge, microwave, oven, stovetop

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

9.6 out of 10, Exceptional, (7)
"This property was exactly what we needed. Perfect location beautiful house very clean and very comfortable. We will definitely return "
The price is AU$513
includes taxes & fees
5 Mar - 6 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
Charming Farmhouse w/ Pool & Fishing Pond!
Fridge, microwave, stovetop, dishwasher

Charming Farmhouse w/ Pool & Fishing Pond!

10.0 out of 10, Exceptional, (9)
"Everything about the house and property was exactly as described. We had the best time there with plenty of space to spread out. It was very clean and comfortable. The kids had so much fun exploring and they visited the ice cream shop everyday that it was open.We will definitely stay here again."
Charming Farmhouse w/ Pool & Fishing Pond!
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Outdoor spa tub

Waterfront Lakehouse in Clinton, CT with Hot Tub!

7.0 out of 10, Good, (2)
"My family and I absolutely loved our stay at this home! It was the perfect retreat for us, and we thoroughly enjoyed the hot tub and the breathtaking sunset views, especially while cooking in the beautifully designed kitchen. The kitchen was fully equipped, making it easy to prepare an amazing family dinner. The town of Clinton was absolutely charming, with the friendliest people, and we fell in love with Hammonasset Beach—it’s a must-visit! We’ll definitely be returning in the summer. The...
Waterfront Lakehouse in Clinton, CT with Hot Tub!
Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
Outdoor dining

Updated Lakefront House *outdoor tv and water toys- 10 min from UConn

10.0 out of 10, Exceptional, (35)
"The perfect get away spot to stay for our wedding weekend! Jena was great and so responsive and helpful!! 💕"
Updated Lakefront House *outdoor tv and water toys- 10 min from UConn
Cozy dog friendly updated house in quiet village adjacent to park
Property grounds

Cozy dog friendly updated house in quiet village adjacent to park

10.0 out of 10, Exceptional, (25)
"The house is pretty nice and there's space for friends to chill and relax"
Cozy dog friendly updated house in quiet village adjacent to park
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
Property grounds

The Bungalow at Eagleville Lake Under 3 miles to UCONN!

10.0 out of 10, Exceptional, (49)
"The house was clean and perfect location for us. The owner had more than enough amenities and offered help in whatever questions I had. We plan to stay here on the regular now for visiting our daughter during her next 3 years. "
The Bungalow at Eagleville Lake Under 3 miles to UCONN!
11 Mi to Powder Ridge Mountain: Connecticut Home
Terrace/patio

11 Mi to Powder Ridge Mountain: Connecticut Home

9.6 out of 10, Exceptional, (4)
"Everything about our stay was flawless. The instructions prior to arrival were complete and clear. The property was clean and stocked with basic necessities. The pool was an added plus.Excellent communication from our gracious hostess."
11 Mi to Powder Ridge Mountain: Connecticut Home
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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Other property types in Portland

Postcard Cabins Machimoodus
Exterior

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (5)
"Loved how tranquil this site is. Was great to disconnect in nature. "
The price is AU$163
includes taxes & fees
4 Mar - 5 Mar
Postcard Cabins Machimoodus
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Living area

NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!

9.4 out of 10, Exceptional, (13)
"I had such a good time here that I actually added three more weeks so this is the first of three reviews as I booked them separately. The host was really nice working with me and the associate that supports any household requests as well. Everything works perfectly, but the host associate was nice to come and anticipate the batteries on the smart lock would be running low and came and changed them along with leaving me extra snow melt, and a shovel after clearing the walkways. The house is well...
NEW: Spacious & Convenient Hideaway!Centrally located & 10 min from airport!
Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is AU$541
includes taxes & fees
20 Feb - 21 Feb
Blue Back Bungalow
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.