Condo vacation rentals in Cumberland

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Popular amenities for Cumberland condo rentals

Weekly condo rentals

Top guest favorite
Condo in East End
4.99 out of 5 average rating, 96 reviews

Charming, newly remodeled space atop Munjoy Hill.

ChrisRating, 5 stars7 months ago
Unit was very clean, situated in a quiet residential area and within walking distance to many of Portland's best bars, restaurants and attractions. Host was communicative and provided clear guidance on check-in/-out procedures and offered up suggestions to local attractions. On my recommended list - dinner at Twelve (one of the best restaurants in the US, IMHO); on-site food truck tacos washed down with a Hazy IPA at Bellflower or Austin Street Brewery; an everything bagel with lox & morning latte at Forage; the East Promenade for a food truck lunch, then a stroll along the waterfront trail to the port area for an ice cream cone at Gorgeous gelato; afternoon coffee at Double Great Coffee; and a post-dinner whiskey @ Independence Ice. Only downside on my visit was the upstairs neighbor. Dude clearly isn't a principal dancer in the Portland Ballet, as light on his feet wouldn't describe him. Not a stereo or TV issue - you can just hear the noise from him walking (8AM-10PM when there)
Guest favorite
Condo in East End
4.93 out of 5 average rating, 74 reviews

Fresh & Modern Family Friendly Central 2 bed

MadeleineRating, 5 stars2 weeks ago
Great apartment very centrally located in Portland - easy to walk everywhere, so close to great coffee shops and restaurants! Apartment was perfect for our family of four, and the pack and play and kid's toys were great! Very family friendly. Highly recommend!
Superhost
Condo in Old Orchard Beach
4.88 out of 5 average rating, 33 reviews

Steps from the sandy beach! "Surf's Up"

KatieRating, 5 stars9 months ago
We enjoyed our stay! The place was very clean. The hosts were responsive and helpful. The train does go right behind the place at an intersection. The horn is very loud, which was hard for our toddler. Just something to consider if you’re traveling with infants/toddlers. Overall, would definitely recommend!
Top guest favorite
Condo in Back Cove
4.99 out of 5 average rating, 69 reviews

Charming 2-Bedroom Back Cove Retreat

MelissaRating, 5 stars1 week ago
This home was just perfect for a few days of R&R for my sister and me. The apartment is perfectly appointed with everything needed for a relaxing and easy stay. Kudos to the designer - the space was the perfect blend of a lovely aesthetic and function. I will certainly be remembering this little gem for the next time I'm in Portland!
Guest favorite
Condo in Portland
4.96 out of 5 average rating, 25 reviews

2-Bedroom Condo Close to Downtown

LinneaRating, 5 stars7 months ago
What a great location for a quiet stay in Portland! It’s 5 minutes by car to the Old Port and easily walkable/runnable to the Back Cove Trail and even to downtown Portland itself. The condo is lovely and just as described. My family (2 adults, 2 kids ages 3 and 7) was very comfortable during our 3-night stay. Lastly, Colin was responsive and a great host.
Superhost
Condo in Old Orchard Beach
4.84 out of 5 average rating, 91 reviews

Downtown Old Orchard beach 1 bedroom

SanjanaRating, 5 stars8 months ago
Amazing location. Very close to the beach. Perfect room! We enjoyed our stay at Mary’s place!
Top guest favorite
Condo in East End
5 out of 5 average rating, 46 reviews

The Observatory Retreat

MarinaRating, 5 stars1 week ago
Excellent location with great restaurants & shops within walking distance, ample street parking, accommodating and friendly hosts, and a clean, bright space stocked with everything we needed for our long weekend in Portland!
Guest favorite
Condo in East End
4.98 out of 5 average rating, 41 reviews

Munjoy Hill One Bedroom Condo - Casco Bay Views

AbbyRating, 5 stars8 months ago
It was a perfect sunny weekend where we spent most of our weekend on Munjoy hill enjoying the restaurants and shops! We walked everywhere and enjoyed the peace and views at Jeffreys place. We were upset we could not extend our stay and take advantage of the late check out that Maggie offered! Easy in and out of the condo! One of our favorite stays in our favorite part of Portland!

Pet-friendly condo rentals

Guest favorite
Condo in Bartlett
4.91 out of 5 average rating, 100 reviews

White Mountains Hiking Dogs Storyland Family

WilliamRating, 5 stars7 months ago
Wife and I had a great time at Fairley’s place. Condo was as advertised, clean with all the utensils you need. The resort has a clubhouse with all great amenities. Location is great! We would definitely like to rent again.
Guest favorite
Condo in Bartlett
4.87 out of 5 average rating, 149 reviews

Spacious Condo-Attitash Ski-Storyland-Saco & More!

CristinRating, 5 stars2 days ago
Beautiful place to stay! Great amenities for the kids ! Will definitely go back ❤️
Guest favorite
Condo in Kennebunk
4.89 out of 5 average rating, 211 reviews

Over 1000 Five Star Reviews! Walk to Dock Square !

BrittanyRating, 5 stars2 weeks ago
We had a wonderful stay over Memorial Day weekend! The location here truly can’t be beat-walking distance to everything Kennebunkport has to offer. We loved that the property was pet friendly and well stocked. The property itself was exactly as described with very comfy beds and a well stocked kitchen. We would absolutely stay here again. Robert and Janette were incredibly responsive with our questions and recommendations and had clear checking and checkout instructions. A true gem of a weekend getaway!
Top guest favorite
Condo in Damariscotta
4.89 out of 5 average rating, 164 reviews

River Escape - Studio Apt. with River Access

MarlaRating, 5 stars1 month ago
Lovely stay in a cozy place during a harrowing move. Cozy place provided just what we needed.
Guest favorite
Condo in Bartlett
4.9 out of 5 average rating, 106 reviews

Bartlett N. Conway, NH condo ski near Storyland

GiovannaRating, 5 stars3 months ago
We loved our stay and couldn't have felt more at home. Condo has everything you need and the hosts were so kind. Plenty of space for our family of 4 but could easily fit 6. Location is ideal for families to explore all Bartlett has to offer. Highly recommend and can't wait to come back!
Superhost
Condo in Brunswick
4.85 out of 5 average rating, 179 reviews

New 2BR 2King beds Private Apt Downtown Brunswick

HannahRating, 5 stars4 weeks ago
Great place to stay in Brunswick! Extremely walkable to the downtown restaurants and shops. Clean and bright space with spacious bedrooms (enough space to throw a pack-and-play in one of the bedrooms). Beds were comfortable and living room/kitchen good for socializing! Bonus — you can also access the Androscoggin River path for a nearby dose of nature and water. This is the second location of Spencer’s we’ve stayed in (the other about two years ago) and both stays were awesome. Highly recommend for a trip to Brunswick!
Guest favorite
Condo in East End
4.9 out of 5 average rating, 92 reviews

Luxurious 2BR Penthouse | Ocean Views | East End

JustinRating, 5 stars2 weeks ago
Wonderful—everything about this place. I loved it and will stay again one day. Fantastic.
Guest favorite
Condo in Glen
4.93 out of 5 average rating, 267 reviews

An Amazing Mountain Getaway!

KelseyRating, 5 stars1 week ago
My family and I had an amazing weekend. Melissa was very responsive and flexible with checking in/out. Everything was clean, plenty of linens and towels, great location, comfy beds. 10/10. We can’t wait to be back!

Condo rentals with a pool

Top guest favorite
Condo in Glen
4.98 out of 5 average rating, 130 reviews

Don’t miss out, book for Fall NOW!

CARISSARating, 5 stars3 months ago
This AirBnB was a perfect winter vacation escape. It had everything we needed for our two families. The kitchen was so well stocked and we were never without. Great set up. My 5 year old begged to live there forever! We can't wait to come back!
Guest favorite
Condo in Wells
4.85 out of 5 average rating, 187 reviews

Two-Bedroom Condo on the Wells/Ogunquit town-line

SusanRating, 5 stars4 days ago
Christopher was a helpful host and his place was perfect! Clean, fully stocked, great location. It was close to lots of beaches and restaurants and the pool was great for the little ones
Guest favorite
Condo in Glen
4.89 out of 5 average rating, 264 reviews

Intimate Garden Style Condo with Mountain Views

MollyRating, 5 stars4 months ago
We had a wonderful stay here! We were up for a weekend to enjoy the snow and mountains and appreciated how close it was to everything we planned. We had a snow storm the second night and the grounds maintenance was perfect, we had no problem walking right out the door. We would recommend heading for a stay!
Guest favorite
Condo in Wells
4.95 out of 5 average rating, 101 reviews

Coastal Condo with Pool at Wells Beach

MaryRating, 5 stars1 month ago
Julie’s place was very nice and very clean. The location was great, right across the street from the ocean. The kitchen was well-equipped and there was even a small basket of treats. Julie responded very quickly to any messages we sent. We would highly recommend this place.
Superhost
Condo in Wells
4.76 out of 5 average rating, 134 reviews

Generic Two Bedroom - Stair access only

DeysiRating, 5 stars2 weeks ago
Great place to stay for our family of 4. I asked for 3 beds and that request was made possible. I enjoyed the area and it was quiet and peaceful place to rest after walking around the beaches and or state parks. Amenities were very good and communication with the check in team was excellent.
Top guest favorite
Condo in Conway
4.96 out of 5 average rating, 110 reviews

Cozy, clean, 2nd floor condo in Conway, NH!

RachelRating, 5 stars5 months ago
A beautiful condo, just 20 minutes away from the heart of North Conway. Everything was in pristine condition and it is always amazing to have a kitchen at our fingertips. Beautiful views of the woods out back. Would definitely recommend to those coming to visit the North Conway, New Hampshire area and surroundings!!!!
Guest favorite
Condo in Conway
4.92 out of 5 average rating, 122 reviews

Cozy Family Retreat with Saco River Access

JeanineRating, 5 stars3 months ago
Our 3rd time staying here....great location and reasonably priced. Love the view out back to the trees and a peek of some mountains. Also great snow cleanup - we were here for a big storm and the plows cleared the car park and the paths were shoveled quickly.
Guest favorite
Condo in Glen
4.95 out of 5 average rating, 124 reviews

Resort Amenities| Amazing Views |Hiking Paradise

GrahamRating, 5 stars1 week ago
We had a great stay here, the condo was clean and host was easy to get a hold of. Probably the best location you can get for visiting the White mountains, centrally located in between Mt Washington and North Conway village. We highly recommend!

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