We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Middlesex Vacation Rentals

Destination
Revenue impacts this sort order. Learn more

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
50 rentals in Middlesex.
Close to 4 ski areas, vacation rental in Middlesex
Close to 4 ski areas, vacation rental in Middlesex
Close to 4 ski areas, vacation rental in Middlesex

Close to 4 ski areas

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The perfect family getaway with stunning views, large deck and hot tub, vacation rental in Middlesex
The perfect family getaway with stunning views, large deck and hot tub, vacation rental in Middlesex
The perfect family getaway with stunning views, large deck and hot tub, vacation rental in Middlesex

The perfect family getaway with stunning views, large deck and hot tub

Rental Home
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The following properties within 20 miles of Middlesex match all your filters:
Clean 3br apt. Historical Waterbury Village. Nearby Stowe and Sugarbush skiing., vacation rental in Middlesex
Clean 3br apt. Historical Waterbury Village. Nearby Stowe and Sugarbush skiing., vacation rental in Middlesex
Clean 3br apt. Historical Waterbury Village. Nearby Stowe and Sugarbush skiing., vacation rental in Middlesex

Clean 3br apt. Historical Waterbury Village. Nearby Stowe and Sugarbush skiing.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Centrally Located w/ easy access to Stowe and MRV, vacation rental in Middlesex
Centrally Located w/ easy access to Stowe and MRV, vacation rental in Middlesex
Centrally Located w/ easy access to Stowe and MRV, vacation rental in Middlesex

Centrally Located w/ easy access to Stowe and MRV

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Great 2 bedroom apartment in Downtown Waterbury, vacation rental in Middlesex
Great 2 bedroom apartment in Downtown Waterbury, vacation rental in Middlesex
Great 2 bedroom apartment in Downtown Waterbury, vacation rental in Middlesex

Great 2 bedroom apartment in Downtown Waterbury

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Artful Stays Mountainview Studio + 1 Bedroom, Montpelier VT, near downtown, vacation rental in Middlesex
Artful Stays Mountainview Studio + 1 Bedroom, Montpelier VT, near downtown, vacation rental in Middlesex
Artful Stays Mountainview Studio + 1 Bedroom, Montpelier VT, near downtown, vacation rental in Middlesex

Artful Stays Mountainview Studio + 1 Bedroom, Montpelier VT, near downtown

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Modern Farmhouse Loft in downtown Waterbury, vacation rental in Middlesex
Modern Farmhouse Loft in downtown Waterbury, vacation rental in Middlesex
Modern Farmhouse Loft in downtown Waterbury, vacation rental in Middlesex

Modern Farmhouse Loft in downtown Waterbury

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Meadows Mountains and more, vacation rental in Middlesex
Meadows Mountains and more, vacation rental in Middlesex
Meadows Mountains and more, vacation rental in Middlesex

Meadows Mountains and more

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spectacular Vermont Views -- In Waterbury/Stowe, vacation rental in Middlesex
Spectacular Vermont Views -- In Waterbury/Stowe, vacation rental in Middlesex
Spectacular Vermont Views -- In Waterbury/Stowe, vacation rental in Middlesex

Spectacular Vermont Views -- In Waterbury/Stowe

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Elegant & renewed mountain-view home with private hot tub, large deck & backyard, vacation rental in Middlesex
Elegant & renewed mountain-view home with private hot tub, large deck & backyard, vacation rental in Middlesex
Elegant & renewed mountain-view home with private hot tub, large deck & backyard, vacation rental in Middlesex

Elegant & renewed mountain-view home with private hot tub, large deck & backyard

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cedar Sweet Apartment, vacation rental in Middlesex
Cedar Sweet Apartment, vacation rental in Middlesex
Cedar Sweet Apartment, vacation rental in Middlesex

Cedar Sweet Apartment

Condo/Apartment
0 bedrooms
0 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Country House Apartment, vacation rental in Middlesex
Country House Apartment, vacation rental in Middlesex
Country House Apartment, vacation rental in Middlesex

Country House Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Artful Stays 1st Fl'r in Civil War Infirmary Home near VCFA+Downtown Montpelier, vacation rental in Middlesex
Artful Stays 1st Fl'r in Civil War Infirmary Home near VCFA+Downtown Montpelier, vacation rental in Middlesex
Artful Stays 1st Fl'r in Civil War Infirmary Home near VCFA+Downtown Montpelier, vacation rental in Middlesex

Artful Stays 1st Fl'r in Civil War Infirmary Home near VCFA+Downtown Montpelier

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Brand New, Modern, Cozy Mountain Guest Suite, vacation rental in Middlesex
Brand New, Modern, Cozy Mountain Guest Suite, vacation rental in Middlesex
Brand New, Modern, Cozy Mountain Guest Suite, vacation rental in Middlesex

Brand New, Modern, Cozy Mountain Guest Suite

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Recreation Retreat, vacation rental in Middlesex
Recreation Retreat, vacation rental in Middlesex
Recreation Retreat, vacation rental in Middlesex

Recreation Retreat

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
3 Covered Bridges Guesthouse 2 bedroom apartment, vacation rental in Middlesex
3 Covered Bridges Guesthouse 2 bedroom apartment, vacation rental in Middlesex
3 Covered Bridges Guesthouse 2 bedroom apartment, vacation rental in Middlesex

3 Covered Bridges Guesthouse 2 bedroom apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Capital City Apartment, vacation rental in Middlesex
Capital City Apartment, vacation rental in Middlesex
Capital City Apartment, vacation rental in Middlesex

Capital City Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mountain Home On 75 Acres With Brooks & Waterfalls In Cent, vacation rental in Middlesex
Mountain Home On 75 Acres With Brooks & Waterfalls In Cent, vacation rental in Middlesex
Mountain Home On 75 Acres With Brooks & Waterfalls In Cent, vacation rental in Middlesex

Mountain Home On 75 Acres With Brooks & Waterfalls In Cent

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Artful Lodging Mountain-view Studio+1 Bedrm Apt in Historic Home, Montpelier VT, vacation rental in Middlesex
Artful Lodging Mountain-view Studio+1 Bedrm Apt in Historic Home, Montpelier VT, vacation rental in Middlesex
Artful Lodging Mountain-view Studio+1 Bedrm Apt in Historic Home, Montpelier VT, vacation rental in Middlesex

Artful Lodging Mountain-view Studio+1 Bedrm Apt in Historic Home, Montpelier VT

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Charming House 7-min walk to downtown Montpelier, vacation rental in Middlesex
Charming House 7-min walk to downtown Montpelier, vacation rental in Middlesex
Charming House 7-min walk to downtown Montpelier, vacation rental in Middlesex

Charming House 7-min walk to downtown Montpelier

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Hunting or Ski Mountain Cabin, vacation rental in Middlesex
Hunting or Ski Mountain Cabin, vacation rental in Middlesex
Hunting or Ski Mountain Cabin, vacation rental in Middlesex

Hunting or Ski Mountain Cabin

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Pine Tree Hideaway - Private Home in the Mad River Valley, vacation rental in Middlesex
Pine Tree Hideaway - Private Home in the Mad River Valley, vacation rental in Middlesex
Pine Tree Hideaway - Private Home in the Mad River Valley, vacation rental in Middlesex

Pine Tree Hideaway - Private Home in the Mad River Valley

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cheerful, old gold in the center of Waterbury historic district, vacation rental in Middlesex
Cheerful, old gold in the center of Waterbury historic district, vacation rental in Middlesex
Cheerful, old gold in the center of Waterbury historic district, vacation rental in Middlesex

Cheerful, old gold in the center of Waterbury historic district

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cottage on the hill with scenic views near historic downtown & close to resorts, vacation rental in Middlesex
Cottage on the hill with scenic views near historic downtown & close to resorts, vacation rental in Middlesex
Cottage on the hill with scenic views near historic downtown & close to resorts, vacation rental in Middlesex

Cottage on the hill with scenic views near historic downtown & close to resorts

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Twin Brook Manse in Cox Brok, vacation rental in Middlesex
Twin Brook Manse in Cox Brok, vacation rental in Middlesex
Twin Brook Manse in Cox Brok, vacation rental in Middlesex

Twin Brook Manse in Cox Brok

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Crossett Hill Lodge: Loft, vacation rental in Middlesex
Crossett Hill Lodge: Loft, vacation rental in Middlesex
Crossett Hill Lodge: Loft, vacation rental in Middlesex

Crossett Hill Lodge: Loft

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Mad River Hideaway, Warren, Vermont, vacation rental in Middlesex
Mad River Hideaway, Warren, Vermont, vacation rental in Middlesex
Mad River Hideaway, Warren, Vermont, vacation rental in Middlesex

Mad River Hideaway, Warren, Vermont

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
New ! Modern Dwell Design near Stowe and Skiing, vacation rental in Middlesex
New ! Modern Dwell Design near Stowe and Skiing, vacation rental in Middlesex
New ! Modern Dwell Design near Stowe and Skiing, vacation rental in Middlesex

New ! Modern Dwell Design near Stowe and Skiing

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
A peaceful & uplifting retreat with AMAZING views in the heart of the mountains., vacation rental in Middlesex
A peaceful & uplifting retreat with AMAZING views in the heart of the mountains., vacation rental in Middlesex
A peaceful & uplifting retreat with AMAZING views in the heart of the mountains., vacation rental in Middlesex

A peaceful & uplifting retreat with AMAZING views in the heart of the mountains.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
The Terraces: Pristine Forest Setting, Between the Resorts, vacation rental in Middlesex
The Terraces: Pristine Forest Setting, Between the Resorts, vacation rental in Middlesex
The Terraces: Pristine Forest Setting, Between the Resorts, vacation rental in Middlesex

The Terraces: Pristine Forest Setting, Between the Resorts

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Perry Hill Escape, vacation rental in Middlesex
Perry Hill Escape, vacation rental in Middlesex
Perry Hill Escape, vacation rental in Middlesex

Perry Hill Escape

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT, vacation rental in Middlesex
Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT, vacation rental in Middlesex
Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT, vacation rental in Middlesex

Artful Lodging & Retreats Civil War Infirmary 2nd Fl'r 3 Bdrm Apt Montpelier VT

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Views, Luxury, Hot Tub, vacation rental in Middlesex
Views, Luxury, Hot Tub, vacation rental in Middlesex
Views, Luxury, Hot Tub, vacation rental in Middlesex

Views, Luxury, Hot Tub

Rental Home
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Large, Comfortable, Retro 1970s Hillside Chalet, vacation rental in Middlesex
Large, Comfortable, Retro 1970s Hillside Chalet, vacation rental in Middlesex
Large, Comfortable, Retro 1970s Hillside Chalet, vacation rental in Middlesex

Large, Comfortable, Retro 1970s Hillside Chalet

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Bright 3 bed 2 bath home!, vacation rental in Middlesex
Bright 3 bed 2 bath home!, vacation rental in Middlesex
Bright 3 bed 2 bath home!, vacation rental in Middlesex

Bright 3 bed 2 bath home!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Montpelier 3 bedroom house located on Terrace St a 5 min walk to downtown., vacation rental in Middlesex
Montpelier 3 bedroom house located on Terrace St a 5 min walk to downtown., vacation rental in Middlesex
Montpelier 3 bedroom house located on Terrace St a 5 min walk to downtown., vacation rental in Middlesex

Montpelier 3 bedroom house located on Terrace St a 5 min walk to downtown.

Rental Home
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Traditional Vermont Ski Chalet Central to Mad River Valley and Stowe, vacation rental in Middlesex
Traditional Vermont Ski Chalet Central to Mad River Valley and Stowe, vacation rental in Middlesex
Traditional Vermont Ski Chalet Central to Mad River Valley and Stowe, vacation rental in Middlesex

Traditional Vermont Ski Chalet Central to Mad River Valley and Stowe

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Secluded Elbow Room in Stunning Foothills, vacation rental in Middlesex
Secluded Elbow Room in Stunning Foothills, vacation rental in Middlesex
Secluded Elbow Room in Stunning Foothills, vacation rental in Middlesex

Secluded Elbow Room in Stunning Foothills

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Majestic Mountain Retreat in Vermont's Recreation Crossroads, vacation rental in Middlesex
Majestic Mountain Retreat in Vermont's Recreation Crossroads, vacation rental in Middlesex
Majestic Mountain Retreat in Vermont's Recreation Crossroads, vacation rental in Middlesex

Majestic Mountain Retreat in Vermont's Recreation Crossroads

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Peaceful Vermont Mountain Retreat on 10 Beautiful Acres, vacation rental in Middlesex
Peaceful Vermont Mountain Retreat on 10 Beautiful Acres, vacation rental in Middlesex
Peaceful Vermont Mountain Retreat on 10 Beautiful Acres, vacation rental in Middlesex

Peaceful Vermont Mountain Retreat on 10 Beautiful Acres

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Beautiful & Spacious Apartment on College Street, vacation rental in Middlesex
Beautiful & Spacious Apartment on College Street, vacation rental in Middlesex
Beautiful & Spacious Apartment on College Street, vacation rental in Middlesex

Beautiful & Spacious Apartment on College Street

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Updated Vermont farmhouse with privacy, views, hot tub, and pool, vacation rental in Middlesex
Updated Vermont farmhouse with privacy, views, hot tub, and pool, vacation rental in Middlesex
Updated Vermont farmhouse with privacy, views, hot tub, and pool, vacation rental in Middlesex

Updated Vermont farmhouse with privacy, views, hot tub, and pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Perry Hill Escape - Luxury Log Cabin in Waterbury, vacation rental in Middlesex
Perry Hill Escape - Luxury Log Cabin in Waterbury, vacation rental in Middlesex
Perry Hill Escape - Luxury Log Cabin in Waterbury, vacation rental in Middlesex

Perry Hill Escape - Luxury Log Cabin in Waterbury

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cozy Modern Farmhouse Near EVERYTHING!!, vacation rental in Middlesex
Cozy Modern Farmhouse Near EVERYTHING!!, vacation rental in Middlesex
Cozy Modern Farmhouse Near EVERYTHING!!, vacation rental in Middlesex

Cozy Modern Farmhouse Near EVERYTHING!!

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Modern home, minutes to Waterbury, Stowe, and Sugarbush, vacation rental in Middlesex
Modern home, minutes to Waterbury, Stowe, and Sugarbush, vacation rental in Middlesex
Modern home, minutes to Waterbury, Stowe, and Sugarbush, vacation rental in Middlesex

Modern home, minutes to Waterbury, Stowe, and Sugarbush

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Spacious Contemporary Dream Home, vacation rental in Middlesex
Spacious Contemporary Dream Home, vacation rental in Middlesex
Spacious Contemporary Dream Home, vacation rental in Middlesex

Spacious Contemporary Dream Home

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Huge Waterbury Home near Stowe Mountain / views & sauna, vacation rental in Middlesex
Huge Waterbury Home near Stowe Mountain / views & sauna, vacation rental in Middlesex
Huge Waterbury Home near Stowe Mountain / views & sauna, vacation rental in Middlesex

Huge Waterbury Home near Stowe Mountain / views & sauna

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Moose Meadow Lodge & Treehouse - Adirondack style log cabin on 86 private acres, vacation rental in Middlesex
Moose Meadow Lodge & Treehouse - Adirondack style log cabin on 86 private acres, vacation rental in Middlesex
Moose Meadow Lodge & Treehouse - Adirondack style log cabin on 86 private acres, vacation rental in Middlesex

Moose Meadow Lodge & Treehouse - Adirondack style log cabin on 86 private acres

Rental Home
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
2 homes, luxury and serenity close to Vt's premier skiing, hiking & gourmet food, vacation rental in Middlesex
2 homes, luxury and serenity close to Vt's premier skiing, hiking & gourmet food, vacation rental in Middlesex
2 homes, luxury and serenity close to Vt's premier skiing, hiking & gourmet food, vacation rental in Middlesex

2 homes, luxury and serenity close to Vt's premier skiing, hiking & gourmet food

Rental Home
2 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
More info
Check in
Check out
As seen on
Vrbo.com logo
Cody's Clubhouse, vacation rental in Middlesex
Cody's Clubhouse, vacation rental in Middlesex
Cody's Clubhouse, vacation rental in Middlesex

Cody's Clubhouse

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
As seen on
HolidayLettings.com logo
Affiliated with FlipKey
Showing results 1-50 of 50