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Upton holiday lettings

We found 43 holiday rentals — enter your dates for availability

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August 2025

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Scroll through and select from holiday rentals in Upton to find one that's perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Upton

Showing deals for:14 Nov - 21 Nov

Steps outside the door. Gorgeous mountains with peak foliage

Exceptional

(19 reviews)

Cozy Cottage in the Great North Woods

Errol, NH

17% off

£138 per night

includes taxes & fees

Exceptional

(17 reviews)

Cozy Lake Front home for Boating, fishing, winter sports, and gorgeous views,

Errol, NH

7% off

£162 per night

includes taxes & fees

Exceptional

(27 reviews)

Adventure Awaits at Our Scenic Farmhouse - on snowmobile trail, ride in/out

Andover, ME

7% off

£175 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

Find the best place to stay - Upton

The Cabin , Umbagog lake area on The Maine / NH border

Sleeps 4 · 1 bedroom · 1 bathroom

The Cove - Beautiful private log home with large deck, fireplace and dock on Lake Umbagog!!

Sleeps 8 · 3 bedrooms · 2 bathrooms

Log cabin~hiking, hunting, skiing, with direct snowmobile trail access.

Sleeps 8 · 3 bedrooms · 1 bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find out more about Upton

Why visit Upton

Outdoor Adventures: Upton is a haven for outdoor enthusiasts, offering stunning national parks and picturesque lakes for exploration.
Romantic Getaways: The serene landscapes provide a perfect backdrop for couples seeking a romantic escape.
Family-Friendly Activities: Enjoy various recreational activities suitable for families amidst beautiful scenery.
Diverse Accommodation: Choose from luxury lodges, charming cabins, or inviting chalets for a delightful stay.
Rich Historical Atmosphere: Discover nearby attractions that showcase Upton's intriguing history and heritage.

Popular types of accommodation in Upton

If you're seeking the perfect getaway in Upton, look no further. Our most popular types of accommodation include charming houses, inviting cabins, and delightful chalets. Whether you're interested in a cosy log cabin, a serene lodge by the lakes, or the best lodges Upton has to offer, we have a range of options to suit your needs. Enjoy your stay with transparency, savings, and reassurance at every turn.

Houses: The top choice for holidaymakers in Upton, offering spacious and comfortable stays for families, couples, or groups.
Cabins: A close second, these rustic retreats provide a cosy atmosphere amidst nature for a truly tranquil experience.
Chalets: These charming lodgings blend comfort with scenic views, perfect for those seeking a touch of elegance.
Condos: Ideal for those who appreciate modern amenities and easy access to local attractions.
Cottages: Quaint and inviting, cottages are a delightful option for a quaint getaway in Upton.**

Top attractions near Upton

Upton, Maine, is a charming destination perfect for outdoor enthusiasts and couples seeking a romantic getaway. Visitors can explore stunning national parks, serene lakes, and picturesque islands, ideal for a beach experience. For those looking for accommodation, there are options ranging from luxury lodges to family campsites, providing a delightful mix of adventure and relaxation amid breathtaking scenery.

Lake Umbagog: A serene lake offering beautiful beaches and stunning scenery, perfect for romantic outings or a peaceful day by the water. Enjoy activities like swimming and picnicking amidst the natural beauty.
Umbagog State Park: This expansive state park invites adventure enthusiasts with its breathtaking outdoor landscapes. Explore hiking trails, wildlife watching, and thrilling activities in a picturesque setting.
Magalloway River: A scenic river ideal for a leisurely day outdoors, providing opportunities for fishing, kayaking, and appreciating the tranquil surroundings of nature.

Things to do recommended for couples

For a romantic getaway in Upton, indulge in the thrill of skiing at the nearby Jordan Mountain, Quantum Leap, or North Peak Express Ski Lifts, all offering stunning views and adventurous vibes. Perfect for couples seeking excitement and a touch of romance in the great outdoors.

Things to do recommended for families

Families visiting Upton, Maine, can enjoy picturesque hikes in the nearby White Mountain National Forest and explore the thrilling activities at Sunday River Resort, perfect for both skiing in winter and mountain biking in summer. Don't miss the chance to visit local farms for fresh produce and engaging farm activities!

Things to do recommended for groups

Groups visiting Upton can hike the scenic Grafton Notch Trailhead, enjoy a round at the Sunday River Golf Club, or explore local produce at the Berlin Farmers Market. Each activity offers a unique blend of outdoor adventure, sport, and local culture.

What do I need to keep in mind when booking a vacation in 'Upton

When travelling with a group, family, pets, or planning for extended stays, it's important to filter your search according to your key priorities. Here are some helpful booking tips for using Vrbo.

Traveling to Upton with a group: Think about how many bedrooms you'll require, along with additional features like a fully equipped kitchen or outdoor areas for group get-togethers. Thankfully, you can easily filter for these options and much more on Vrbo.
Traveling to Upton with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, such as a private swimming pool. Additionally, considering your closeness to family-friendly attractions is wise.
Taking your pets with you to Upton: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Upton: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Upton

Upton, Maine, offers a charming escape for those seeking picturesque outdoor adventures and romantic getaways. Nestled amidst the stunning Devon countryside, visitors can explore the serene Upton Lakes and enjoy family-friendly recreational activities. Nearby attractions showcase a rich historical atmosphere, perfect for a memorable holiday experience. Whether you're wandering through the scenic landscapes or relishing the tranquil beauty, Upton promises an idyllic retreat for every traveller.

Errol: Situated 5.6km from Upton, Errol is a charming city that invites outdoor enthusiasts and couples seeking a romantic getaway. Renowned for its stunning scenery, Errol is an ideal destination for skiing aficionados, with excellent ski fields and resorts nearby. Nature lovers will appreciate the picturesque landscapes surrounding the area, including tranquil lakes, majestic mountains, and the breathtaking national state park that beckons exploration. Whether you're hitting the slopes or enjoying a leisurely stroll by the water, Errol promises a delightful travel experience.
Cambridge: Located a mere 3.7km from Upton, Cambridge is a vibrant city perfect for those seeking adventure and outdoor activities. The city is surrounded by beautiful lakes and a captivating national state park, making it a haven for nature lovers and thrill-seekers alike. Whether you fancy a day of hiking, kayaking, or exploring the local theme park, Cambridge offers a range of attractions that cater to all interests. With its scenic vistas and opportunities for outdoor fun, this city is a must-visit on your itinerary.
North Oxford: Just 6.2km from Upton, North Oxford is a delightful destination for those craving both romance and outdoor experiences. This picturesque locale is known for its ski resorts, offering winter sports enthusiasts ample opportunities to enjoy the snow. With a backdrop of beautiful lakes and a local stadium hosting various events, North Oxford combines scenic beauty with fun activities. Whether you're enjoying a day of skiing or attending a lively event, North Oxford provides a charming setting for a memorable holiday.

Best time to go to Upton

If you're planning a trip to Upton, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and August, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	14.4°F (-9.8°C)	Light Rain	Mostly Cloudy	Low	Slightly High
February	16.5°F (-8.6°C)	Light Rain	Mostly Cloudy	Low	Slightly High
March	25.0°F (-3.9°C)	Light Rain	Mostly Cloudy	Average	Average
April	36.9°F (2.7°C)	Light Rain	Mostly Cloudy	High	Average
May	51.1°F (10.6°C)	Light Rain	Mostly Cloudy	High	Slightly Low
June	59.0°F (15.0°C)	Light Rain	Mostly Cloudy	Average	Average
July	65.3°F (18.5°C)	Light Rain	Mostly Sunny	Average	Average
August	63.5°F (17.5°C)	Light Rain	Mostly Sunny	High	Average
September	56.5°F (13.6°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	44.6°F (7.0°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
November	32.0°F (0.0°C)	Light Rain	Mostly Cloudy	Low	Average
December	21.7°F (-5.7°C)	Light Rain	Mostly Cloudy	Average	Slightly High

Booking with Vrbo is a breeze

Are you aiming to save on your next getaway? It might be worth considering some flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the ideal Vrbo property that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient space for you to plan new adventures, carry on with your existing arrangements, or review and organise your bookings. The properties you've saved or reserved are now neatly categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Choose a holiday rental for your Upton getaway

Learn about the unique charm of Upton with a stay in a holiday home rental. This city has something for everyone. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Upton

Do you want to discover top things to see and do in the city? Venture out of your holiday home and check out everything that makes Upton a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Sunday River Golf Club (15.5 mi / 25 km)
Sunday River (17 mi / 27.4 km)

Exploring the natural features in Upton

Whether you're looking for fun outdoor activities or just want to take in the scenery, Upton is a great place to get out in nature. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

Lake Umbagog (6.4 mi / 10.3 km)
Magalloway River (11.2 mi / 18 km)
Angel Falls (16 mi / 25.7 km)
Sunday River (17.3 mi / 27.8 km)
Mooselookmeguntic Lake (19.1 mi / 30.7 km)
Howard Pond (19.3 mi / 31.1 km)

Frequently asked questions

What is the best area to stay in Upton when booking a holiday rental?

When considering a holiday rental in Upton, Maine, the best area to stay is near the picturesque Androscoggin River. This charming locale offers a serene environment, ideal for those seeking a tranquil escape. The proximity to the river provides ample opportunities for outdoor activities such as fishing, kayaking, and hiking along the scenic trails.

Another appealing option is the vicinity to the White Mountain National Forest, which is just a short drive away. This area is great for nature enthusiasts, offering breathtaking views, hiking trails, and the chance to experience the stunning fall foliage. Staying here not only immerses you in the beauty of nature but also places you close to some well-known attractions like the scenic Kancamagus Highway, renowned for its spectacular vistas.

How much does it cost to rent a holiday home in Upton?

Prices for holiday rentals in Upton vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Upton to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.

Are there any discounts for Upton holiday house rentals?

You can find great discounts on house rentals in Upton on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.

Can I find long-stay holiday rentals in Upton?

A long-stay holiday rental in Upton is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

Are there any Upton holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Upton with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.

When is the best time to visit Upton for a holiday rental?

April marks the beginning of the peak season in Upton, Maine, attracting visitors eager to immerse themselves in the stunning natural beauty of the region. This time of year heralds the arrival of spring, with blooming flowers and warming temperatures, making it superb for outdoor activities such as hiking, fishing, and exploring the scenic countryside.

As the weather becomes increasingly pleasant, daytime temperatures typically range from 10 to 15 degrees Celsius, creating a comfortable environment for sightseeing and engaging with Upton's lovely landscapes. The areas around Upton offer numerous trails and picturesque spots, ideal for both leisurely strolls and adventurous hikes, allowing you to fully soak in the charm of Maine's wilderness.

For those looking to enjoy a more budget-friendly experience, consider visiting in February. While this is a quieter time, it offers a unique charm with the snow-covered landscapes superb for winter sports enthusiasts, including snowshoeing and cross-country skiing.

How early should I book a Upton holiday rental?

Book your Upton holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.

Can I change or cancel my Upton home rental booking on Vrbo?

To find Upton holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.

Why should I join Vrbo as a host?

Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Upton holiday rental prices shown on Vrbo?

Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.