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Upton Holiday Rentals

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50 rentals in Upton.
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Mountain Cottage - Lake and Mountain Views!, holiday rental in Upton

Mountain Cottage - Lake and Mountain Views!

1 bedroom
1 bathroom
Sleeps 4
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Beautiful private log home with large deck, fireplace and dock on Lake Umbagog!!, holiday rental in Upton

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

3 bedrooms
2 bathrooms
Sleeps 10
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Beautiful Off-the-Grid Cabin. Next to A.T. in Andover Notch., holiday rental in Upton

Beautiful Off-the-Grid Cabin. Next to A.T. in Andover Notch.

2 bedrooms
1 bathroom
Sleeps 6
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Off-the-Grid Easy Access Cabin to the A.T. in Andover Notch ., holiday rental in Upton

Off-the-Grid Easy Access Cabin to the A.T. in Andover Notch .

2 bedrooms
1 bathroom
Sleeps 6
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The Cabin  Maine / New Hampshire border, holiday rental in Upton

The Cabin Maine / New Hampshire border

1 bedroom
1 bathroom
Sleeps 5
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Cottage on Akers Pond, holiday rental in Upton

Cottage on Akers Pond

2 bedrooms
1 bathroom
Sleeps 6
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True North at Sunday River  4 Miles to Lodge  In Desirable Powder Ridge, holiday rental in Upton

True North at Sunday River 4 Miles to Lodge In Desirable Powder Ridge

4 bedrooms
3 bathrooms
Sleeps 12
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Secluded Off-grid Mountain Cabin | Panoramic Views | ATV or Hike from Cabin, holiday rental in Upton

Secluded Off-grid Mountain Cabin | Panoramic Views | ATV or Hike from Cabin

2 bedrooms
1 bathroom
Sleeps 4
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Good for the Soul log cabin!!!, holiday rental in Upton

Good for the Soul log cabin!!!

3 bedrooms
1 bathroom
Sleeps 6
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Lakefront Home...Snowmobiling Right From Your Front Door!, holiday rental in Upton

Lakefront Home...Snowmobiling Right From Your Front Door!

2 bedrooms
2 bathrooms
Sleeps 6
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THE MANSION on 5 Acres Overlooking Sunday River, holiday rental in Upton

THE MANSION on 5 Acres Overlooking Sunday River

6 bedrooms
3 bathrooms
Sleeps 15
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Direct Snowmobile Access:  Cozy 3 Bed 2 Bath Cape, holiday rental in Upton

Direct Snowmobile Access: Cozy 3 Bed 2 Bath Cape

3 bedrooms
2 bathrooms
Sleeps 9
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Book 2 Midweek Nights, Get The 3rd Free | The Keystone Cabin at Sunday River, holiday rental in Upton

Book 2 Midweek Nights, Get The 3rd Free | The Keystone Cabin at Sunday River

4 bedrooms
4 bathrooms
Sleeps 14
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Brookside Cabin - Hampshire Woods, holiday rental in Upton

Brookside Cabin - Hampshire Woods

2 bedrooms
2 bathrooms
Sleeps 8
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3 minute drive to Sunday River Ski Resort. Stunning views!, holiday rental in Upton

3 minute drive to Sunday River Ski Resort. Stunning views!

6 bedrooms
2 bathrooms
Sleeps 12
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Beautiful Akers Pond!!!, holiday rental in Upton

Beautiful Akers Pond!!!

3 bedrooms
2 bathrooms
Sleeps 8
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Elegant home with mountain views, grill, and wrap-around deck!, holiday rental in Upton

Elegant home with mountain views, grill, and wrap-around deck!

5 bedrooms
4 bathrooms
Sleeps 12
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Ski in, ski out! Direct access to Sunday River Resort, holiday rental in Upton

Ski in, ski out! Direct access to Sunday River Resort

7 bedrooms
10 bathrooms
Sleeps 32
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Secluded chalet w/ upscale interior & jetted tub, close to Sunday River Resort!, holiday rental in Upton

Secluded chalet w/ upscale interior & jetted tub, close to Sunday River Resort!

3 bedrooms
3 bathrooms
Sleeps 8
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Secluded pet friendly house w/ hot tub and BBQ. 15 minute to Sunday River, holiday rental in Upton

Secluded pet friendly house w/ hot tub and BBQ. 15 minute to Sunday River

3 bedrooms
2 bathrooms
Sleeps 8
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Less than 2 mi to Sunday River - on 2 acres flat land!, holiday rental in Upton

Less than 2 mi to Sunday River - on 2 acres flat land!

3 bedrooms
2 bathrooms
Sleeps 10
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Adorable Cottage in Mountain Village | ATV Trail Access | Remote kayaking nearby, holiday rental in Upton

Adorable Cottage in Mountain Village | ATV Trail Access | Remote kayaking nearby

1 bedroom
1 bathroom
Sleeps 4
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Spacious ski lodge w/ cathedral ceilings & incredible game room w/mountain views, holiday rental in Upton

Spacious ski lodge w/ cathedral ceilings & incredible game room w/mountain views

4 bedrooms
2 bathrooms
Sleeps 13
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Amazing Maine Get-Away - Maine's Western Mountains, holiday rental in Upton

Amazing Maine Get-Away - Maine's Western Mountains

16 bedrooms
7 bathrooms
Sleeps 32
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Newry condo w/ ski-in/ski-out access to trails, shared heated pool!, holiday rental in Upton

Newry condo w/ ski-in/ski-out access to trails, shared heated pool!

3 bedrooms
2 bathrooms
Sleeps 8
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Secluded and Elegant - Mountain Retreat with peaceful Sunday River Road Setting, holiday rental in Upton

Secluded and Elegant - Mountain Retreat with peaceful Sunday River Road Setting

5 bedrooms
4 bathrooms
Sleeps 14
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Ski-in/ski-out condo with shared pool & hot tub! Just steps away from ski lift!, holiday rental in Upton

Ski-in/ski-out condo with shared pool & hot tub! Just steps away from ski lift!

1 bedroom
1 bathroom
Sleeps 6
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3 Minutes To Ski Lifts With Fantastic Views!, holiday rental in Upton

3 Minutes To Ski Lifts With Fantastic Views!

1 bedroom
1 bathroom
Sleeps 4
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Family Friendly Vacation Log Home Nestled In Powder Ridge.  5 Minute Ride To Ski, holiday rental in Upton

Family Friendly Vacation Log Home Nestled In Powder Ridge. 5 Minute Ride To Ski

3 bedrooms
2 bathrooms
Sleeps 10
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Mountain condo w/ a shared indoor hot tub & pool - ski-in/ski-out access!, holiday rental in Upton

Mountain condo w/ a shared indoor hot tub & pool - ski-in/ski-out access!

1 bedroom
1 bathroom
Sleeps 6
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Mountainside condo w/ ski-in/ski-out access, shared heated pool, & more!, holiday rental in Upton

Mountainside condo w/ ski-in/ski-out access, shared heated pool, & more!

1 bedroom
1 bathroom
Sleeps 4
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Cozy condo w/ ski-in/ski-out access to trails, heated pool, hot tub, & more!, holiday rental in Upton

Cozy condo w/ ski-in/ski-out access to trails, heated pool, hot tub, & more!

1 bedroom
1 bathroom
Sleeps 5
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Mountain views with comforts of home. 5 minute drive to mountain!, holiday rental in Upton

Mountain views with comforts of home. 5 minute drive to mountain!

3 bedrooms
3 bathrooms
Sleeps 6
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On-Mountain Ski Chalet - Sleeps 18 - Ping Pong, Hot Tub, Quick Walk to Slopes, holiday rental in Upton

On-Mountain Ski Chalet - Sleeps 18 - Ping Pong, Hot Tub, Quick Walk to Slopes

6 bedrooms
5 bathrooms
Sleeps 20
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Boyd, holiday rental in Upton

Boyd

4 bedrooms
2 bathrooms
Sleeps 8
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German Style Chalet in Newry Maine. Close to hiking, skiing and XC, holiday rental in Upton

German Style Chalet in Newry Maine. Close to hiking, skiing and XC

4 bedrooms
3 bathrooms
Sleeps 12
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Huge Lakefront Cabin | Sleeps 12| King Bed| Dock| Ski Saddleback| Snowmobile|, holiday rental in Upton

Huge Lakefront Cabin | Sleeps 12| King Bed| Dock| Ski Saddleback| Snowmobile|

5 bedrooms
3 bathrooms
Sleeps 12
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Luxury Sunday River Ski & Snowboard Home! - 10 Bedrooms, 2 Hot Tubs & Much More!, holiday rental in Upton

Luxury Sunday River Ski & Snowboard Home! - 10 Bedrooms, 2 Hot Tubs & Much More!

10 bedrooms
11 bathrooms
Sleeps 26
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Incredible Estate w/ Movie Theater, Pool, Arcade, Sauna, Billiards, Etc.Golf Ski, holiday rental in Upton

Incredible Estate w/ Movie Theater, Pool, Arcade, Sauna, Billiards, Etc.Golf Ski

9 bedrooms
8 bathrooms
Sleeps 26
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Ski-in/ski-out condo w/ mountain views & access to a shared pool & hot tub!, holiday rental in Upton

Ski-in/ski-out condo w/ mountain views & access to a shared pool & hot tub!

1 bedroom
1 bathroom
Sleeps 4
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Memory Lane Vacations  ~ Cozy Country Mobile Home, holiday rental in Upton

Memory Lane Vacations ~ Cozy Country Mobile Home

2 bedrooms
1 bathroom
Sleeps 6
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Halls on Mooselookmeguntic, holiday rental in Upton

Halls on Mooselookmeguntic

4 bedrooms
4 bathrooms
Sleeps 10
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Loon Landing, holiday rental in Upton

Loon Landing

3 bedrooms
1 bathroom
Sleeps 6
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Memory Lane Vacations ~ Four seasons in Western ME, holiday rental in Upton

Memory Lane Vacations ~ Four seasons in Western ME

0 bedrooms
1 bathroom
Sleeps 7
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Tree House, holiday rental in Upton

Tree House

3 bedrooms
1 bathroom
Sleeps 5
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Year Round Family Vacation Getaway, holiday rental in Upton

Year Round Family Vacation Getaway

5 bedrooms
3 bathrooms
Sleeps 16
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Luxury Estate w/ Movie Theater, Pool, Arcade, Sauna, Billiards, Golf, Ski, etc, holiday rental in Upton

Luxury Estate w/ Movie Theater, Pool, Arcade, Sauna, Billiards, Golf, Ski, etc

9 bedrooms
8 bathrooms
Sleeps 26
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Large Custom Log Home. Spacious, family-friendly and close to Sunday River, holiday rental in Upton

Large Custom Log Home. Spacious, family-friendly and close to Sunday River

5 bedrooms
3 bathrooms
Sleeps 12
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Spacious, Newly Built Home with hot tub/large deck close to Sunday River Ski Res, holiday rental in Upton

Spacious, Newly Built Home with hot tub/large deck close to Sunday River Ski Res

4 bedrooms
3 bathrooms
Sleeps 10
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Berlin Trails Inn and Farm, holiday rental in Upton

Berlin Trails Inn and Farm

3 bedrooms
1 bathroom
Sleeps 8
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