Photo by Robbie Martin

Upton Holiday Rentals

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Holiday Rentals in Upton

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

10.0 out of 10, Exceptional, (40)
"Absolutely amazing property! The hosts are gracious and very quick to reply to you. Will definitely be back!"
INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space

9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

10.0 out of 10, Exceptional, (26)
"Fun"
9 Bedroom Estate, Sleeps 24, Heated Pool, Hot Tub, Movie Theater, Game Room

Peaceful Lakefront Cabin w/ amazing views and sauna; minutes to skiing

10.0 out of 10, Exceptional, (16)
"Had such an amazing and relaxing time here. The property is beautiful and the sauna is an added plus!"
Peaceful Lakefront Cabin w/ amazing views and sauna; minutes to skiing

Luxury Log Cabin near Sunday River: Panoramic Mountain Views & Hot Tub

10.0 out of 10, Exceptional, (22)
"We spent a considerable amount of time searching through listings to find the perfect location for a family vacation, and Nikki and John's luxury cabin did not disappoint! This home has a number of wonderful amenities, including a hot tub, outdoor fire pit, gas fire table, gas fireplace, large screen televisions on multiple floors, games, and even a shuffle board table! The home was spotless, the kitchen was extremely well appointed, the beds were comfortable, there was plenty of hot water, and...
Luxury Log Cabin near Sunday River: Panoramic Mountain Views & Hot Tub

The Mansion- Exclusive Private Estate on 5 Pristine Acres

10.0 out of 10, Exceptional, (33)
"The house was AMAZING! Had a wonderful time We had a pretty big group and the house was comfortable enough for all of us including kids and a dog. Did not feel crowded at all. Hosts were wonderful, very accommodating with late check out and asking if we need anything. The views from the house are spectacular, you dont need to go out at all honestly, you would have a good time just enjoying the house amenities and the views, def worth the drive from NY"
The Mansion- Exclusive Private Estate on 5 Pristine Acres

Mainestay | 4 Bed, 2 Bath

9.8 out of 10, Exceptional, (20)
"Great stay, house was clean upon arrival and had plenty of extras to make for a fun long weekend up near Sunday River. Will definitely come again."
Mainestay | 4 Bed, 2 Bath

Cozy Cottage in the Great North Woods

9.2 out of 10, Wonderful, (16)
"Cute little cabin, very comfy beds!"
The price is AU$364
includes taxes & fees
1 Dec - 2 Dec
Cozy Cottage in the Great North Woods

Crystal Falls Retreat, Swimming, Fishing, ATV

9.8 out of 10, Exceptional, (224)
"The home offers an absolutely stunning view of Crystal Falls. During our stay, we went hinking to the Giant Falls, Devil's Slide, Artitist Bluff, and Sabbaday Falls. It was a memorable stay for all of us (two adults and one dog)."
Crystal Falls Retreat, Swimming, Fishing, ATV

Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

10.0 out of 10, Exceptional, (3)
"The house was extremely well stocked and well organized. Caroline was a great and communicative host checking in and ensuring everything went well as necessary throughout our stay. There was more than enough room for everyone in our group of 14 to sleep. Plenty of great games both indoor and outdoor at the house. The local area guide was a very useful addition as well. "
Sleeps 20 | Hot Tub | Game Room | Fire Pit |4500SF

Majestic Views & Nature Lovers! Kayaking, ATVing, Snowmobiling, Fishing, Hiking!

8.6 out of 10, Excellent, (17)
"We loved having our morning coffee out on the porch. "
Majestic Views & Nature Lovers! Kayaking, ATVing, Snowmobiling, Fishing, Hiking!

Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

10.0 out of 10, Exceptional, (111)
"The house and set up was great for us and 4 kids! Yard space to play, cards and games to play inside, the hot tub was fun, the walk path through the woods to the river was well marked but short. The only down side was the river was full blown river like, steep way down, deep and quick. The pictures were not the same to what is behind the property with no access, rocks, or low points to the water for any type of enjoyment. Otherwise, we had a great time, with a well equiped house with everything...
Riverfront Ski Chalet Cabin only minutes to Sunday River Resort & Trails Galore!

Mountainside Chalet direct views of Sunday River

9.2 out of 10, Wonderful, (29)
"Amazing spot with everything you need and what’s spectacular view!"
Mountainside Chalet direct views of Sunday River

Stunning view of Sunday River, Luxurious Home, Hot Tub, Games, Ski

10.0 out of 10, Exceptional, (75)
"We had a great time staying at this property. The house was well stocked and had everything that we needed. The views from the living rooms and decks were outstanding and created a wonderful backdrop for a relaxing weekend. "
Stunning view of Sunday River, Luxurious Home, Hot Tub, Games, Ski

Lakefront Cabin w/ sauna: minutes to Saddleback skiing and snowmobile trails

10.0 out of 10, Exceptional, (10)
"This property has great proximity to Rangeley Lake with a really nice view from the living room and porch. Heaters worked well. We had the property to ourselves during the week. Close to town and great restaurants."
Lakefront Cabin w/ sauna: minutes to Saddleback skiing and snowmobile trails

90 Second, Traffic-Free Drive to Sunday River

10.0 out of 10, Exceptional, (13)
"A lovely clean place that would be wonderful for families with children! We couldn’t be closer to Sunday River!!"
90 Second, Traffic-Free Drive to Sunday River

NEW! Views! HotTub! FirePlace! Arcade Game! Sleeps 11

10.0 out of 10, Exceptional, (5)
"Very nice property not far from the center of Bethel. The host had great communication and the check-in process very easy with number coded door locks. Nice hot tub and spacious yard. We brought had our dog with us and it was good to see that floors were plenty durable. The arcade game was fun for the kids & parents! We found that the beds were very comfortable and likely the best beds we had in all the rentals through Vrbo over the years. Would definitely come back here again."
NEW! Views! HotTub! FirePlace! Arcade Game! Sleeps 11

🐾Gray Wulff - This rustic dog friendly camp sits on the shore of Quimby Pond

9.6 out of 10, Exceptional, (19)
"It was a delightful 3 days of fly fishing and woodland solitude."
🐾Gray Wulff - This rustic dog friendly camp sits on the shore of Quimby Pond

JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.

9.8 out of 10, Exceptional, (125)
"Family reunion location with plenty of space! Great hot tub and amenities!"
JORDAN RUN -Minutes To Mountain. Hot Tub, Fireplace, Fire Pit, Pet Friendly.

Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

8.4 out of 10, Very good, (49)
"Great location and nice place."
Dog-Friendly Slopeside Condo - Walk to Slopes - Fireplace, Firepit & WiFi

Duck Out on Rangeley Lake

8.4 out of 10, Very good, (5)
"Had fun. Rental met needs and was as described. "
Duck Out on Rangeley Lake
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 types of properties in Upton you may be interested in

Jordan Hotel

3.0 star property
8.4 out of 10, Very good, (250)
"The employees were super friendly and helpful, and the mocktails were very yumy.."
The price is AU$313
includes taxes & fees
1 Dec - 2 Dec
Jordan Hotel

Snow Cap Inn

2.5 star property
8.6 out of 10, Excellent, (225)
"Beautiful place with carved pillars, unique furnitures and deco. The stuff is super friendly and nice. They provide all the stuff for marshmallow roasting at the fire pit near the pool. The only problem we had is to find the place at night. Our GPS guided us to a nearby property which was closed at the time. Later on we found out that we need use the name of the property instead of the address of the property for GPS to guide us to the right place. "
Snow Cap Inn

Grand Summit Hotel

3.0 star property
8.0 out of 10, Very good, (220)
"Amazing stay at Grand Summit. Staff were extremely friendly and helpful. After hitting the slopes for Sunday River's "not really opening day" on Halloween the hot tub and sauna were a radical way to rejuvenate. The cuisine at the on site restaurant "Camp" was superb. Highly recommend the cheesy short rib fries. "
The price is AU$377
includes taxes & fees
1 Dec - 2 Dec
Grand Summit Hotel
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Upton?

Yes, there are holiday rentals close to the most popular sights in Upton, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upton has to offer?

INDOOR POOL, HOT TUB, PRIVATE 86 acre Retreat and Event Space: This holiday home rental outside of Upton is located on a river, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Upton?

While you're exploring the area, Umbagog State Park and Lake Umbagog are a couple of picturesque spots to get outside and enjoy nature. Grafton Notch State Park and Angel Falls are a couple of places you'll find in the wider area.

What are holiday rentals like in Upton?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upton. Holiday rentals feature extras such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.