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Holiday Rentals in Middlebury

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
50 rentals in Middlebury.
Beautiful 4-Bedroom Home beside Middlebury College, holiday rental in Middlebury
Beautiful 4-Bedroom Home beside Middlebury College, holiday rental in Middlebury
Beautiful 4-Bedroom Home beside Middlebury College, holiday rental in Middlebury

Beautiful 4-Bedroom Home beside Middlebury College

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury, holiday rental in Middlebury
Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury, holiday rental in Middlebury
Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury, holiday rental in Middlebury

Great Location! Cozy Two Bedroom Apartment in the Heart of Middlebury

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Middlebury, VT Newly renovated four bedroom  Luxury Home  (sleeps 8), holiday rental in Middlebury
Middlebury, VT Newly renovated four bedroom  Luxury Home  (sleeps 8), holiday rental in Middlebury
Middlebury, VT Newly renovated four bedroom  Luxury Home  (sleeps 8), holiday rental in Middlebury

Middlebury, VT Newly renovated four bedroom Luxury Home (sleeps 8)

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Middlebury Home with Sunset views!, holiday rental in Middlebury
Middlebury Home with Sunset views!, holiday rental in Middlebury
Middlebury Home with Sunset views!, holiday rental in Middlebury

Middlebury Home with Sunset views!

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★FAST Wifi★HOT TUB  ★PET FRIENDLY, holiday rental in Middlebury
CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★FAST Wifi★HOT TUB  ★PET FRIENDLY, holiday rental in Middlebury
CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★FAST Wifi★HOT TUB  ★PET FRIENDLY, holiday rental in Middlebury

CHIC DOWNTOWN COTTAGE ★UBER WALKABLE ★FAST Wifi★HOT TUB ★PET FRIENDLY

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Newly renovated East Middlebury Apartment miles from Middlebury College, holiday rental in Middlebury
Newly renovated East Middlebury Apartment miles from Middlebury College, holiday rental in Middlebury
Newly renovated East Middlebury Apartment miles from Middlebury College, holiday rental in Middlebury

Newly renovated East Middlebury Apartment miles from Middlebury College

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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River House in the Heart of Middlebury, holiday rental in Middlebury
River House in the Heart of Middlebury, holiday rental in Middlebury
River House in the Heart of Middlebury, holiday rental in Middlebury

River House in the Heart of Middlebury

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury
Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury
Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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In the heart of town, a modern farmhouse, holiday rental in Middlebury
In the heart of town, a modern farmhouse, holiday rental in Middlebury
In the heart of town, a modern farmhouse, holiday rental in Middlebury

In the heart of town, a modern farmhouse

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury
Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury
Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, holiday rental in Middlebury

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
More info
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River House in the Heart of Middlebury, holiday rental in Middlebury
River House in the Heart of Middlebury, holiday rental in Middlebury
River House in the Heart of Middlebury, holiday rental in Middlebury

River House in the Heart of Middlebury

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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October Specials in the most beautiful time of year 5 minutes from downtown, holiday rental in Middlebury
October Specials in the most beautiful time of year 5 minutes from downtown, holiday rental in Middlebury
October Specials in the most beautiful time of year 5 minutes from downtown, holiday rental in Middlebury

October Specials in the most beautiful time of year 5 minutes from downtown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Sun-filled, quiet country home on 27 acres with mountain views, holiday rental in Middlebury
Sun-filled, quiet country home on 27 acres with mountain views, holiday rental in Middlebury
Sun-filled, quiet country home on 27 acres with mountain views, holiday rental in Middlebury

Sun-filled, quiet country home on 27 acres with mountain views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
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Middlebury VT - gorgeous home, holiday rental in Middlebury
Middlebury VT - gorgeous home, holiday rental in Middlebury
Middlebury VT - gorgeous home, holiday rental in Middlebury

Middlebury VT - gorgeous home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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The following properties within 32 kms of Middlebury match all your filters:
Classic Vermont Cabin on 2.5 acres Lake Frontage, holiday rental in Middlebury
Classic Vermont Cabin on 2.5 acres Lake Frontage, holiday rental in Middlebury
Classic Vermont Cabin on 2.5 acres Lake Frontage, holiday rental in Middlebury

Classic Vermont Cabin on 2.5 acres Lake Frontage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Gem on Lake Dunmore sleeps 8 easily, holiday rental in Middlebury
Gem on Lake Dunmore sleeps 8 easily, holiday rental in Middlebury
Gem on Lake Dunmore sleeps 8 easily, holiday rental in Middlebury

Gem on Lake Dunmore sleeps 8 easily

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Doc's Lake house 1st floor, 2 bedroom apartment, holiday rental in Middlebury
Doc's Lake house 1st floor, 2 bedroom apartment, holiday rental in Middlebury
Doc's Lake house 1st floor, 2 bedroom apartment, holiday rental in Middlebury

Doc's Lake house 1st floor, 2 bedroom apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Romantic 1-Bdrm on Lake Dunmore, Views, Linens, Beach, Marina, Pub, Sleeps 4, holiday rental in Middlebury
Romantic 1-Bdrm on Lake Dunmore, Views, Linens, Beach, Marina, Pub, Sleeps 4, holiday rental in Middlebury
Romantic 1-Bdrm on Lake Dunmore, Views, Linens, Beach, Marina, Pub, Sleeps 4, holiday rental in Middlebury

Romantic 1-Bdrm on Lake Dunmore, Views, Linens, Beach, Marina, Pub, Sleeps 4

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Family Friendly Near River  -  Campfires! Hot Tub, Game Rm, Views Pets welcome, holiday rental in Middlebury
Family Friendly Near River  -  Campfires! Hot Tub, Game Rm, Views Pets welcome, holiday rental in Middlebury
Family Friendly Near River  -  Campfires! Hot Tub, Game Rm, Views Pets welcome, holiday rental in Middlebury

Family Friendly Near River - Campfires! Hot Tub, Game Rm, Views Pets welcome

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cottage * Waterhouses, holiday rental in Middlebury
Cottage * Waterhouses, holiday rental in Middlebury
Cottage * Waterhouses, holiday rental in Middlebury

Cottage * Waterhouses

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy cottage with views of Lake Dunmore and mountains, holiday rental in Middlebury
Cozy cottage with views of Lake Dunmore and mountains, holiday rental in Middlebury
Cozy cottage with views of Lake Dunmore and mountains, holiday rental in Middlebury

Cozy cottage with views of Lake Dunmore and mountains

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator., holiday rental in Middlebury
The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator., holiday rental in Middlebury
The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator., holiday rental in Middlebury

The Cabana, a Studio apt. w/ private deck on Lake Dunmore w/ beach. Generator.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Family friendly getaway on Lake Dunmore, holiday rental in Middlebury
Family friendly getaway on Lake Dunmore, holiday rental in Middlebury
Family friendly getaway on Lake Dunmore, holiday rental in Middlebury

Family friendly getaway on Lake Dunmore

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming cabin overlooking Lake Dunmore with stunning views of the Green Mts., holiday rental in Middlebury
Charming cabin overlooking Lake Dunmore with stunning views of the Green Mts., holiday rental in Middlebury
Charming cabin overlooking Lake Dunmore with stunning views of the Green Mts., holiday rental in Middlebury

Charming cabin overlooking Lake Dunmore with stunning views of the Green Mts.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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A cozy apartment suite by the mountain with stunning views, holiday rental in Middlebury
A cozy apartment suite by the mountain with stunning views, holiday rental in Middlebury
A cozy apartment suite by the mountain with stunning views, holiday rental in Middlebury

A cozy apartment suite by the mountain with stunning views

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Relax at our Cottage on Lake Dunmore/Middlebury, holiday rental in Middlebury
Relax at our Cottage on Lake Dunmore/Middlebury, holiday rental in Middlebury
Relax at our Cottage on Lake Dunmore/Middlebury, holiday rental in Middlebury

Relax at our Cottage on Lake Dunmore/Middlebury

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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2 Bdrm on Lake Dunmore, linens, Views, Beach, Marina, Pub, Store. Pet friendly, holiday rental in Middlebury
2 Bdrm on Lake Dunmore, linens, Views, Beach, Marina, Pub, Store. Pet friendly, holiday rental in Middlebury
2 Bdrm on Lake Dunmore, linens, Views, Beach, Marina, Pub, Store. Pet friendly, holiday rental in Middlebury

2 Bdrm on Lake Dunmore, linens, Views, Beach, Marina, Pub, Store. Pet friendly

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Beautiful brand new 1-bedroom apt with gorgeous views, holiday rental in Middlebury
Beautiful brand new 1-bedroom apt with gorgeous views, holiday rental in Middlebury
Beautiful brand new 1-bedroom apt with gorgeous views, holiday rental in Middlebury

Beautiful brand new 1-bedroom apt with gorgeous views

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Keewaydin Suite * Waterhouses, holiday rental in Middlebury
Keewaydin Suite * Waterhouses, holiday rental in Middlebury
Keewaydin Suite * Waterhouses, holiday rental in Middlebury

Keewaydin Suite * Waterhouses

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Guest House surrounded by national forest, holiday rental in Middlebury
Guest House surrounded by national forest, holiday rental in Middlebury
Guest House surrounded by national forest, holiday rental in Middlebury

Guest House surrounded by national forest

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Cozy and pristine timberframe cabin, holiday rental in Middlebury
Cozy and pristine timberframe cabin, holiday rental in Middlebury
Cozy and pristine timberframe cabin, holiday rental in Middlebury

Cozy and pristine timberframe cabin

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Adorable cabin with screened porch and private fire pit, holiday rental in Middlebury
Adorable cabin with screened porch and private fire pit, holiday rental in Middlebury
Adorable cabin with screened porch and private fire pit, holiday rental in Middlebury

Adorable cabin with screened porch and private fire pit

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Private pet-friendly cabin in the woods w/ private campfire pit & screened porch, holiday rental in Middlebury
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch, holiday rental in Middlebury
Private pet-friendly cabin in the woods w/ private campfire pit & screened porch, holiday rental in Middlebury

Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest, holiday rental in Middlebury
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest, holiday rental in Middlebury
Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest, holiday rental in Middlebury

Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lake Front Cottage with great beach and swimming.  Afternoon sun, great sunsets., holiday rental in Middlebury
Lake Front Cottage with great beach and swimming.  Afternoon sun, great sunsets., holiday rental in Middlebury
Lake Front Cottage with great beach and swimming.  Afternoon sun, great sunsets., holiday rental in Middlebury

Lake Front Cottage with great beach and swimming. Afternoon sun, great sunsets.

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Inviting timber frame cabin in Vermont's Green Mountains, holiday rental in Middlebury
Inviting timber frame cabin in Vermont's Green Mountains, holiday rental in Middlebury
Inviting timber frame cabin in Vermont's Green Mountains, holiday rental in Middlebury

Inviting timber frame cabin in Vermont's Green Mountains

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming and meticulously cleaned cabin with panoramic view of the Green Mtns, holiday rental in Middlebury
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns, holiday rental in Middlebury
Charming and meticulously cleaned cabin with panoramic view of the Green Mtns, holiday rental in Middlebury

Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Immaculate mountain cabin with awe inspiring sunrise and mountain views, holiday rental in Middlebury
Immaculate mountain cabin with awe inspiring sunrise and mountain views, holiday rental in Middlebury
Immaculate mountain cabin with awe inspiring sunrise and mountain views, holiday rental in Middlebury

Immaculate mountain cabin with awe inspiring sunrise and mountain views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Cozy home with views of and access to Lake Dunmore, holiday rental in Middlebury
Cozy home with views of and access to Lake Dunmore, holiday rental in Middlebury
Cozy home with views of and access to Lake Dunmore, holiday rental in Middlebury

Cozy home with views of and access to Lake Dunmore

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Peaceful riverfront elegance, holiday rental in Middlebury
Peaceful riverfront elegance, holiday rental in Middlebury
Peaceful riverfront elegance, holiday rental in Middlebury

Peaceful riverfront elegance

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Peaceful House ~ Mountain Views ~ Mins To Middlebury, Flex Cancellation Policy, holiday rental in Middlebury
Peaceful House ~ Mountain Views ~ Mins To Middlebury, Flex Cancellation Policy, holiday rental in Middlebury
Peaceful House ~ Mountain Views ~ Mins To Middlebury, Flex Cancellation Policy, holiday rental in Middlebury

Peaceful House ~ Mountain Views ~ Mins To Middlebury, Flex Cancellation Policy

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Private Green Mountain get-away with pond in Ripton*, holiday rental in Middlebury
Private Green Mountain get-away with pond in Ripton*, holiday rental in Middlebury
Private Green Mountain get-away with pond in Ripton*, holiday rental in Middlebury

Private Green Mountain get-away with pond in Ripton*

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Custom Home in Cornwall - 5 Minutes to Middlebury College, holiday rental in Middlebury
Custom Home in Cornwall - 5 Minutes to Middlebury College, holiday rental in Middlebury
Custom Home in Cornwall - 5 Minutes to Middlebury College, holiday rental in Middlebury

Custom Home in Cornwall - 5 Minutes to Middlebury College

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Charming Guest Barn Cornwall, VT near Middlebury College, holiday rental in Middlebury
Charming Guest Barn Cornwall, VT near Middlebury College, holiday rental in Middlebury
Charming Guest Barn Cornwall, VT near Middlebury College, holiday rental in Middlebury

Charming Guest Barn Cornwall, VT near Middlebury College

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful country home 10 minutes from downtown Middlebury, Vermont., holiday rental in Middlebury
Beautiful country home 10 minutes from downtown Middlebury, Vermont., holiday rental in Middlebury
Beautiful country home 10 minutes from downtown Middlebury, Vermont., holiday rental in Middlebury

Beautiful country home 10 minutes from downtown Middlebury, Vermont.

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Modernized, open style, waterfront lakehouse!  Sleeps up to 10!  Great swimming!, holiday rental in Middlebury
Modernized, open style, waterfront lakehouse!  Sleeps up to 10!  Great swimming!, holiday rental in Middlebury
Modernized, open style, waterfront lakehouse!  Sleeps up to 10!  Great swimming!, holiday rental in Middlebury

Modernized, open style, waterfront lakehouse! Sleeps up to 10! Great swimming!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Cozy One Story Home Surrounded by Mountain Views, Trees near Middlebury College, holiday rental in Middlebury
Cozy One Story Home Surrounded by Mountain Views, Trees near Middlebury College, holiday rental in Middlebury
Cozy One Story Home Surrounded by Mountain Views, Trees near Middlebury College, holiday rental in Middlebury

Cozy One Story Home Surrounded by Mountain Views, Trees near Middlebury College

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful 1805 renovated farmhouse, holiday rental in Middlebury
Beautiful 1805 renovated farmhouse, holiday rental in Middlebury
Beautiful 1805 renovated farmhouse, holiday rental in Middlebury

Beautiful 1805 renovated farmhouse

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Large And Luxurious Farmhouse - Close To Town And College!, holiday rental in Middlebury
Large And Luxurious Farmhouse - Close To Town And College!, holiday rental in Middlebury
Large And Luxurious Farmhouse - Close To Town And College!, holiday rental in Middlebury

Large And Luxurious Farmhouse - Close To Town And College!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
More info
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River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms, holiday rental in Middlebury
River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms, holiday rental in Middlebury
River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms, holiday rental in Middlebury

River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Showing results 1-50 of 50
Frequently Asked Questions about Middlebury