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Middleton Holiday Rentals

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49 rentals in Middleton.
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Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard, holiday rental in Middleton

Countryside Beauty - Min to Madison/Perfect for families/Events&Dogs! Lrg yard

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Free Breakfast. Pool and Hot Tub. Downtown Location. Your Next Vacation!, holiday rental in Middleton

Free Breakfast. Pool and Hot Tub. Downtown Location. Your Next Vacation!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Free Breakfast. Pool and Hot Tub. Downtown Location. Close to the University of, holiday rental in Middleton

Free Breakfast. Pool and Hot Tub. Downtown Location. Close to the University of

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Free Breakfast. Pool and Hot Tub. Downtown Location. Your Next Trip!, holiday rental in Middleton

Free Breakfast. Pool and Hot Tub. Downtown Location. Your Next Trip!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Clarance Gonstead Guest Cottage, Prairie Style, Stone & Tide Water Cypress, holiday rental in Middleton

Clarance Gonstead Guest Cottage, Prairie Style, Stone & Tide Water Cypress

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Pleasant Retreat For 1, 2, or 3 Couples, holiday rental in Middleton

A Pleasant Retreat For 1, 2, or 3 Couples

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Rustic Luxury Awaits In This Beautiful Full Log Lodge On 44 Private Acres, holiday rental in Middleton

Rustic Luxury Awaits In This Beautiful Full Log Lodge On 44 Private Acres

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Madison, WI One Level House With Large Fenced In Yard, holiday rental in Middleton

Madison, WI One Level House With Large Fenced In Yard

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Original cozy farmhouse homestead 2 blocks from the bike path and, holiday rental in Middleton

Original cozy farmhouse homestead 2 blocks from the bike path and

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stay in Safety | Escape to fresh air and lots of space!, holiday rental in Middleton

Stay in Safety | Escape to fresh air and lots of space!

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Conveniently Located On Madison's West Side(just Off University Ave.), holiday rental in Middleton

Conveniently Located On Madison's West Side(just Off University Ave.)

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Amazing townhouse, amazing attractions, amazing city!, holiday rental in Middleton

Amazing townhouse, amazing attractions, amazing city!

2 bedrooms
1 bathroom
Sleeps 4
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Madison/Stoughton 3 BR/3 BA Lake  Kegonsa Cottage, holiday rental in Middleton

Madison/Stoughton 3 BR/3 BA Lake Kegonsa Cottage

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Lake Kegonsa 1BR Cottage 15 Min.to Madison,Sleeps 3 ,Kayaks, holiday rental in Middleton

Lake Kegonsa 1BR Cottage 15 Min.to Madison,Sleeps 3 ,Kayaks

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Private modern retreat on Lake Wisconsin w/ breathtaking views from every window, holiday rental in Middleton

Private modern retreat on Lake Wisconsin w/ breathtaking views from every window

3 bedrooms
2 bathrooms
Sleeps 6
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Private Condo 6 min To Epic, On Ice Age Trail, 13 mi to Capitol, holiday rental in Middleton

Private Condo 6 min To Epic, On Ice Age Trail, 13 mi to Capitol

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful White Barn, holiday rental in Middleton

Beautiful White Barn

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Great Location On Lake Waubesa, 10 Minutes from Downtown Madison and UW campus, holiday rental in Middleton

Great Location On Lake Waubesa, 10 Minutes from Downtown Madison and UW campus

2 bedrooms
1 bathroom
Sleeps 5
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Small Cottage.... Huge  Lake Views!, holiday rental in Middleton

Small Cottage.... Huge Lake Views!

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Two Bedroom Cottage with Great Lake Views!, holiday rental in Middleton

Two Bedroom Cottage with Great Lake Views!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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SPACIOUS LUXURY HOME - CONVENIENT MADISON EAST LOCATION, holiday rental in Middleton

SPACIOUS LUXURY HOME - CONVENIENT MADISON EAST LOCATION

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Madison 3 BR Cottage on 3000 acre Lake. Kayaks & Pontoon, holiday rental in Middleton

Madison 3 BR Cottage on 3000 acre Lake. Kayaks & Pontoon

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Walk to the Alliant Energy Center!  Great for Badger game day weekends!, holiday rental in Middleton

Walk to the Alliant Energy Center! Great for Badger game day weekends!

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront cabin Madison lakes.  kayaks, paddle boards,  and lakeside hot tub, holiday rental in Middleton

Lakefront cabin Madison lakes. kayaks, paddle boards, and lakeside hot tub

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Social Distance in Our Gorgeous, Private Retreat in the Woods, holiday rental in Middleton

Social Distance in Our Gorgeous, Private Retreat in the Woods

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Madison Arboretum Mid-Century Ranch Fireplace, Screen Porch

0 bedrooms
0 bathrooms
Sleeps 0
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Cozy Sandwood Cottage on WI River-pets welcome!, holiday rental in Middleton

Cozy Sandwood Cottage on WI River-pets welcome!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lakefront Living in Madison, holiday rental in Middleton

Lakefront Living in Madison

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Kegonsa cedar efficiency cottage, holiday rental in Middleton

Lake Kegonsa cedar efficiency cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cottage Sweet, holiday rental in Middleton

Cottage Sweet

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lake Wisconsin Family Lake Home with great views, beach access, pier., holiday rental in Middleton

Lake Wisconsin Family Lake Home with great views, beach access, pier.

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Full Log Lodge on 44 Acres, holiday rental in Middleton

Beautiful Full Log Lodge on 44 Acres

5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Jennifer’s & Dave’s Dream house!!, holiday rental in Middleton

Jennifer’s & Dave’s Dream house!!

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Full Bed 102 - THE LITTLE VILLAGE, holiday rental in Middleton

Full Bed 102 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Queen Room 109 - THE LITTLE VILLAGE, holiday rental in Middleton

Queen Room 109 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Queen Room 111 - THE LITTLE VILLAGE, holiday rental in Middleton

Queen Room 111 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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2 Full Beds 101 - THE LITTLE VILLAGE, holiday rental in Middleton

2 Full Beds 101 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Sunniva Inn B&B, holiday rental in Middleton

Sunniva Inn B&B

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Full Bed 105 - THE LITTLE VILLAGE, holiday rental in Middleton

Full Bed 105 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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2 Full Beds 104 - THE LITTLE VILLAGE, holiday rental in Middleton

2 Full Beds 104 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Full Bed 108 - THE LITTLE VILLAGE, holiday rental in Middleton

Full Bed 108 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Queen Room 110 - THE LITTLE VILLAGE, holiday rental in Middleton

Queen Room 110 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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2 Full Beds 107 - THE LITTLE VILLAGE, holiday rental in Middleton

2 Full Beds 107 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Full Bed 106 - THE LITTLE VILLAGE, holiday rental in Middleton

Full Bed 106 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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McFarland Home Near Lakes - 4 Mi to Madison!, holiday rental in Middleton

McFarland Home Near Lakes - 4 Mi to Madison!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Full Bed 103 - THE LITTLE VILLAGE, holiday rental in Middleton

Full Bed 103 - THE LITTLE VILLAGE

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Baehr Haus Downtown Sun Prairie (Room 2&3), holiday rental in Middleton

Baehr Haus Downtown Sun Prairie (Room 2&3)

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Lake Kegonsa Home w/ Fire Pit & Outdoor Oasis!, holiday rental in Middleton

Lake Kegonsa Home w/ Fire Pit & Outdoor Oasis!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lake Home - Huge Yard, Deck & Porch -Minutes to Downtown Madison, holiday rental in Middleton

Beautiful Lake Home - Huge Yard, Deck & Porch -Minutes to Downtown Madison

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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