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Holiday Rentals in Middleton

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Bedrooms

Bathrooms

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5 km
49 rentals in Middleton.
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!, holiday rental in Middleton
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!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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, holiday rental in Middleton
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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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, holiday rental in Middleton
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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Free Breakfast. Pool. Downtown Location. Great for Business Travelers!, holiday rental in Middleton
Free Breakfast. Pool. Downtown Location. Great for Business Travelers!, holiday rental in Middleton
Free Breakfast. Pool. Downtown Location. Great for Business Travelers!, holiday rental in Middleton

Free Breakfast. Pool. Downtown Location. Great for Business Travelers!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Free Breakfast. Pool and Hot Tub. Downtown Area, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Area, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Area, holiday rental in Middleton

Free Breakfast. Pool and Hot Tub. Downtown Area

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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!, holiday rental in Middleton
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!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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King Suite | Free Breakfast. Pool and Hot Tub, holiday rental in Middleton
King Suite | Free Breakfast. Pool and Hot Tub, holiday rental in Middleton
King Suite | Free Breakfast. Pool and Hot Tub, holiday rental in Middleton

King Suite | Free Breakfast. Pool and Hot Tub

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton
Free Breakfast. Pool and Hot Tub. Downtown Location. Near the University of, holiday rental in Middleton

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

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Elegant home w/ well-equipped kitchen, big yard, & many entertainment options, holiday rental in Middleton
Elegant home w/ well-equipped kitchen, big yard, & many entertainment options, holiday rental in Middleton
Elegant home w/ well-equipped kitchen, big yard, & many entertainment options, holiday rental in Middleton

Elegant home w/ well-equipped kitchen, big yard, & many entertainment options

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Very Luxurious and Secluded Home on 4 acres - Great for Cross Fit Games 2023!, holiday rental in Middleton
Very Luxurious and Secluded Home on 4 acres - Great for Cross Fit Games 2023!, holiday rental in Middleton
Very Luxurious and Secluded Home on 4 acres - Great for Cross Fit Games 2023!, holiday rental in Middleton

Very Luxurious and Secluded Home on 4 acres - Great for Cross Fit Games 2023!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Contemporary home in quiet neighborhood with pool & great back yard close to all, holiday rental in Middleton
Contemporary home in quiet neighborhood with pool & great back yard close to all, holiday rental in Middleton
Contemporary home in quiet neighborhood with pool & great back yard close to all, holiday rental in Middleton

Contemporary home in quiet neighborhood with pool & great back yard close to all

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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The following properties within 32 kms of Middleton match all your filters:
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.), holiday rental in Middleton
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.)

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Private & Modern Garden Level Apartment, Hot Tub,  Conservancy access out back!, holiday rental in Middleton
Private & Modern Garden Level Apartment, Hot Tub,  Conservancy access out back!, holiday rental in Middleton
Private & Modern Garden Level Apartment, Hot Tub,  Conservancy access out back!, holiday rental in Middleton

Private & Modern Garden Level Apartment, Hot Tub, Conservancy access out back!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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3 BR 2 BA Townhouse - Great for families or groups!, holiday rental in Middleton
3 BR 2 BA Townhouse - Great for families or groups!, holiday rental in Middleton
3 BR 2 BA Townhouse - Great for families or groups!, holiday rental in Middleton

3 BR 2 BA Townhouse - Great for families or groups!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
More info
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Pool with Slide. Great for Business Travelers!, holiday rental in Middleton
Pool with Slide. Great for Business Travelers!, holiday rental in Middleton
Pool with Slide. Great for Business Travelers!, holiday rental in Middleton

Pool with Slide. Great for Business Travelers!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton

Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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King Suite. Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!, holiday rental in Middleton

King Suite. Free Breakfast. Pool with a Slide. Near Olbrich Botanical Gardens!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Liberty Valley Short Term Rental - 27, holiday rental in Middleton
Liberty Valley Short Term Rental - 27, holiday rental in Middleton
Liberty Valley Short Term Rental - 27, holiday rental in Middleton

Liberty Valley Short Term Rental - 27

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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As seen on
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Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton

Free Breakfast. Pool with a Slide. Your Next Trip!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
As seen on
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Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!, holiday rental in Middleton

Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
As seen on
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King Suite. Free Breakfast. Pool with a Slide. Great for Business Travelers!, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Great for Business Travelers!, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Great for Business Travelers!, holiday rental in Middleton

King Suite. Free Breakfast. Pool with a Slide. Great for Business Travelers!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check-in
Check-out
As seen on
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Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton
Free Breakfast. Pool with a Slide. Your Next Trip!, holiday rental in Middleton

Free Breakfast. Pool with a Slide. Your Next Trip!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Check-out
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King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical, holiday rental in Middleton
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical, holiday rental in Middleton

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Walk to hospital&campus|Free parking|w/ desk&workspace!, holiday rental in Middleton
Walk to hospital&campus|Free parking|w/ desk&workspace!, holiday rental in Middleton
Walk to hospital&campus|Free parking|w/ desk&workspace!, holiday rental in Middleton

Walk to hospital&campus|Free parking|w/ desk&workspace!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Jacuzzi Loft-1Br w/bike-Extnd Stay-Near Capitol!, holiday rental in Middleton
Jacuzzi Loft-1Br w/bike-Extnd Stay-Near Capitol!, holiday rental in Middleton
Jacuzzi Loft-1Br w/bike-Extnd Stay-Near Capitol!, holiday rental in Middleton

Jacuzzi Loft-1Br w/bike-Extnd Stay-Near Capitol!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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30 Day Minimum. Entire House, A/C, Washer & Dryer, holiday rental in Middleton
30 Day Minimum. Entire House, A/C, Washer & Dryer, holiday rental in Middleton
30 Day Minimum. Entire House, A/C, Washer & Dryer, holiday rental in Middleton

30 Day Minimum. Entire House, A/C, Washer & Dryer

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Jacuzzi 1BR loft w/ den/office-open concept, holiday rental in Middleton
Jacuzzi 1BR loft w/ den/office-open concept, holiday rental in Middleton
Jacuzzi 1BR loft w/ den/office-open concept, holiday rental in Middleton

Jacuzzi 1BR loft w/ den/office-open concept

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cute house close to hospital, UW, shops, bike trails and restaurants, holiday rental in Middleton
Cute house close to hospital, UW, shops, bike trails and restaurants, holiday rental in Middleton
Cute house close to hospital, UW, shops, bike trails and restaurants, holiday rental in Middleton

Cute house close to hospital, UW, shops, bike trails and restaurants

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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30 Day Minimum. Entire House. Washer & Dryer. A/C., holiday rental in Middleton
30 Day Minimum. Entire House. Washer & Dryer. A/C., holiday rental in Middleton
30 Day Minimum. Entire House. Washer & Dryer. A/C., holiday rental in Middleton

30 Day Minimum. Entire House. Washer & Dryer. A/C.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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30 Day Minimum. Entire House, Deck, close to Hosp., holiday rental in Middleton
30 Day Minimum. Entire House, Deck, close to Hosp., holiday rental in Middleton
30 Day Minimum. Entire House, Deck, close to Hosp., holiday rental in Middleton

30 Day Minimum. Entire House, Deck, close to Hosp.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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30 Day Minimum. Entire House. Washer/Dryer. A/C., holiday rental in Middleton
30 Day Minimum. Entire House. Washer/Dryer. A/C., holiday rental in Middleton
30 Day Minimum. Entire House. Washer/Dryer. A/C., holiday rental in Middleton

30 Day Minimum. Entire House. Washer/Dryer. A/C.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Renovated Cape Cod w/ King Bed ➕️ � trail proximity, holiday rental in Middleton
Renovated Cape Cod w/ King Bed ➕️ � trail proximity, holiday rental in Middleton
Renovated Cape Cod w/ King Bed ➕️ � trail proximity, holiday rental in Middleton

Renovated Cape Cod w/ King Bed ➕️ � trail proximity

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Madison Arboretum Mid-Century Ranch Screen Porch, Fireplace, holiday rental in Middleton
Madison Arboretum Mid-Century Ranch Screen Porch, Fireplace, holiday rental in Middleton
Madison Arboretum Mid-Century Ranch Screen Porch, Fireplace, holiday rental in Middleton

Madison Arboretum Mid-Century Ranch Screen Porch, Fireplace

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Westside Gem with Sauna and Movie Theatre, holiday rental in Middleton
Westside Gem with Sauna and Movie Theatre, holiday rental in Middleton
Westside Gem with Sauna and Movie Theatre, holiday rental in Middleton

Westside Gem with Sauna and Movie Theatre

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Madison West Side. Luxurious Living 1 Block from Lake., holiday rental in Middleton
Madison West Side. Luxurious Living 1 Block from Lake., holiday rental in Middleton
Madison West Side. Luxurious Living 1 Block from Lake., holiday rental in Middleton

Madison West Side. Luxurious Living 1 Block from Lake.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Gorgeous MCM Ranch, Fantastic Location, 5 Min to UW Campus and Downtown Madison, holiday rental in Middleton
Gorgeous MCM Ranch, Fantastic Location, 5 Min to UW Campus and Downtown Madison, holiday rental in Middleton
Gorgeous MCM Ranch, Fantastic Location, 5 Min to UW Campus and Downtown Madison, holiday rental in Middleton

Gorgeous MCM Ranch, Fantastic Location, 5 Min to UW Campus and Downtown Madison

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Best Location in the Heart of Madison!! Pet-Friendly and Perfect for Remote Work, holiday rental in Middleton
Best Location in the Heart of Madison!! Pet-Friendly and Perfect for Remote Work, holiday rental in Middleton
Best Location in the Heart of Madison!! Pet-Friendly and Perfect for Remote Work, holiday rental in Middleton

Best Location in the Heart of Madison!! Pet-Friendly and Perfect for Remote Work

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious & Secluded Madison Home Near Dtwn!, holiday rental in Middleton
Spacious & Secluded Madison Home Near Dtwn!, holiday rental in Middleton
Spacious & Secluded Madison Home Near Dtwn!, holiday rental in Middleton

Spacious & Secluded Madison Home Near Dtwn!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Fully remodeled ranch close to the southwest bike trail, holiday rental in Middleton
Fully remodeled ranch close to the southwest bike trail, holiday rental in Middleton
Fully remodeled ranch close to the southwest bike trail, holiday rental in Middleton

Fully remodeled ranch close to the southwest bike trail

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hillside Harbor Retreat in Hawks Woods Estates - by University Ridge & Epic, holiday rental in Middleton
Hillside Harbor Retreat in Hawks Woods Estates - by University Ridge & Epic, holiday rental in Middleton
Hillside Harbor Retreat in Hawks Woods Estates - by University Ridge & Epic, holiday rental in Middleton

Hillside Harbor Retreat in Hawks Woods Estates - by University Ridge & Epic

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Modern Shorewood Hills Home, holiday rental in Middleton
Modern Shorewood Hills Home, holiday rental in Middleton
Modern Shorewood Hills Home, holiday rental in Middleton

Modern Shorewood Hills Home

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison, holiday rental in Middleton
Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison, holiday rental in Middleton
Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison, holiday rental in Middleton

Perfect For Large Groups And Families ~ 7.1 Miles From UW Madison

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Luxurious Mid-Century Modern close to Camp Randall Stadium, holiday rental in Middleton
Luxurious Mid-Century Modern close to Camp Randall Stadium, holiday rental in Middleton
Luxurious Mid-Century Modern close to Camp Randall Stadium, holiday rental in Middleton

Luxurious Mid-Century Modern close to Camp Randall Stadium

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Fabulous home backing up to Ice Age Park and Tyrol Basin Skiing, holiday rental in Middleton
Fabulous home backing up to Ice Age Park and Tyrol Basin Skiing, holiday rental in Middleton
Fabulous home backing up to Ice Age Park and Tyrol Basin Skiing, holiday rental in Middleton

Fabulous home backing up to Ice Age Park and Tyrol Basin Skiing

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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�Luxury Home With Outdoor Hottub and Movie Theater For Sale or Rent, holiday rental in Middleton
�Luxury Home With Outdoor Hottub and Movie Theater For Sale or Rent, holiday rental in Middleton
�Luxury Home With Outdoor Hottub and Movie Theater For Sale or Rent, holiday rental in Middleton

�Luxury Home With Outdoor Hottub and Movie Theater For Sale or Rent

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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7500 sq ft home on wooded acres.  Just minutes from west and downtown Madison, holiday rental in Middleton
7500 sq ft home on wooded acres.  Just minutes from west and downtown Madison, holiday rental in Middleton
7500 sq ft home on wooded acres.  Just minutes from west and downtown Madison, holiday rental in Middleton

7500 sq ft home on wooded acres. Just minutes from west and downtown Madison

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Liberty Valley Short Term Rental - 29, holiday rental in Middleton
Liberty Valley Short Term Rental - 29, holiday rental in Middleton
Liberty Valley Short Term Rental - 29, holiday rental in Middleton

Liberty Valley Short Term Rental - 29

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Showing results 1-49 of 49
Frequently Asked Questions about Middleton