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Middlebury Vacation Rentals

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50 rentals in Middlebury.
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Middlebury VT - gorgeous home, vacation rental in Middlebury

Middlebury VT - gorgeous home

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Downtown Middlebury 3 Bedroom Home - Walk Everywhere!, vacation rental in Middlebury

Downtown Middlebury 3 Bedroom Home - Walk Everywhere!

3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Waterfront Ponds,  Beautiful  , 51 Acre Property Retreat, vacation rental in Middlebury

Waterfront Ponds, Beautiful , 51 Acre Property Retreat

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Classic Vermont Cabin On 2.5 Acres With Lake Frontage, vacation rental in Middlebury

Classic Vermont Cabin On 2.5 Acres With Lake Frontage

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sleeps 4: Ski-in/ski-out, vacation rental in Middlebury

Sleeps 4: Ski-in/ski-out

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Lake Front Home with Stunning Views, vacation rental in Middlebury

Lake Front Home with Stunning Views

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Snowcreek Condo at Sugarbush Resort-2 beds/2 baths, slopeside, vacation rental in Middlebury

Snowcreek Condo at Sugarbush Resort-2 beds/2 baths, slopeside

2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Breathtaking New Lake Champlain Beach,Ski Escape!, vacation rental in Middlebury

Breathtaking New Lake Champlain Beach,Ski Escape!

1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Premier Ski in Ski out Mountainside Condo - Pet Friendly, vacation rental in Middlebury

Premier Ski in Ski out Mountainside Condo - Pet Friendly

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Ski On/Ski Off 1 Bedroom Condo, vacation rental in Middlebury

Ski On/Ski Off 1 Bedroom Condo

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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VT VACATION PARADISE - Lake Champlain Perfect 4 LG GROUPS/ 3 cottages Available!, vacation rental in Middlebury

VT VACATION PARADISE - Lake Champlain Perfect 4 LG GROUPS/ 3 cottages Available!

3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Sugarbush Mountainside Retreat - Ski In Ski Out, vacation rental in Middlebury

Sugarbush Mountainside Retreat - Ski In Ski Out

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!, vacation rental in Middlebury

Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Great cottage to unplug and relax on the lake - Sleeps 6, vacation rental in Middlebury

Great cottage to unplug and relax on the lake - Sleeps 6

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Romantic 1-Bdrm on Lake Dunmore, Views, Linens, Beach, Marina, Pub, Sleeps 4, vacation rental in Middlebury

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

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Lake Champlain, vacation rental in Middlebury

Charming Lake Champlain

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Guest House, vacation rental in Middlebury

Waterfront Guest House

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Mountainside single-family home just steps from Sugarbush Resort., vacation rental in Middlebury

Mountainside single-family home just steps from Sugarbush Resort.

6 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Lake Champlain Vacation Home - Summer Avalability: Dock, Decks & Private Beach, vacation rental in Middlebury

Lake Champlain Vacation Home - Summer Avalability: Dock, Decks & Private Beach

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cozy, dog-friendly cottage near a creek w/ a furnished deck & forest views, vacation rental in Middlebury

Cozy, dog-friendly cottage near a creek w/ a furnished deck & forest views

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mountainside Condo at Sugarbush Vt Walk to the Resort!, vacation rental in Middlebury

Mountainside Condo at Sugarbush Vt Walk to the Resort!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Log Cabin w/ Mountain Views near Lake, vacation rental in Middlebury

Spectacular Log Cabin w/ Mountain Views near Lake

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic log cabin on a pond w/ mountain views, deck & pool table - dogs OK!, vacation rental in Middlebury

Classic log cabin on a pond w/ mountain views, deck & pool table - dogs OK!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Bright, Open Loft Condo at Sugarbush, vacation rental in Middlebury

Bright, Open Loft Condo at Sugarbush

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW to VRBO! Stunning 3 Bedroom Lake House/SkiHouse!, vacation rental in Middlebury

NEW to VRBO! Stunning 3 Bedroom Lake House/SkiHouse!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Unique Modern Sugarbush Condo with Mountain Views, vacation rental in Middlebury

Unique Modern Sugarbush Condo with Mountain Views

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Little House Vermont, vacation rental in Middlebury

The Little House Vermont

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Cottage * Waterhouses, vacation rental in Middlebury

Cottage * Waterhouses

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Frosty Lane Escape is a cozy rural getaway, yet close enough to any attractions!, vacation rental in Middlebury

Frosty Lane Escape is a cozy rural getaway, yet close enough to any attractions!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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River Stone Lodge MTN Views, River, Hiking, Hot Tub, WIFI, Campfires, 4 bedrooms, vacation rental in Middlebury

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

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Sugarbush Mouintain Home, vacation rental in Middlebury

Charming Sugarbush Mouintain Home

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace, vacation rental in Middlebury

Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Large And Luxurious Farmhouse - Close To Town And College!, vacation rental in Middlebury

Large And Luxurious Farmhouse - Close To Town And College!

4 bedrooms
5 bathrooms
Sleeps 13
Match: Sleeps
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Keewaydin Suite * Waterhouses, vacation rental in Middlebury

Keewaydin Suite * Waterhouses

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beauty, Comfort  & Quality - 4 Bedroom Home in the Midst of Vermont's Splendor, vacation rental in Middlebury

Beauty, Comfort & Quality - 4 Bedroom Home in the Midst of Vermont's Splendor

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated Condo at Lincoln Peak Sugarbush, vacation rental in Middlebury

Newly Renovated Condo at Lincoln Peak Sugarbush

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Watch Point Inn & Cottages/Lake Champlain/Addison CountyVT, Great Fishing Access, vacation rental in Middlebury

Watch Point Inn & Cottages/Lake Champlain/Addison CountyVT, Great Fishing Access

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mountain view home in the treetops w/ forest views, deck & fireplace!, vacation rental in Middlebury

Mountain view home in the treetops w/ forest views, deck & fireplace!

4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Spectacular views on Lake Champlain, vacation rental in Middlebury

Spectacular views on Lake Champlain

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming One Bedroom Cottage Steps from the Water's Edge, vacation rental in Middlebury

Charming One Bedroom Cottage Steps from the Water's Edge

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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1888 3 story Farmhouse w/ great views 15 min. from Midd campus, vacation rental in Middlebury

1888 3 story Farmhouse w/ great views 15 min. from Midd campus

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Cozy Mountain Yurt on Organic Farm, vacation rental in Middlebury

Cozy Mountain Yurt on Organic Farm

0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sugarbush Snow Creek Condo: Slopeside 2 Bed/2 Bath, vacation rental in Middlebury

Sugarbush Snow Creek Condo: Slopeside 2 Bed/2 Bath

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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19 Mountainside, vacation rental in Middlebury

19 Mountainside

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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16 Village Run, vacation rental in Middlebury

16 Village Run

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Mountainview mansion with patio, balcony, wood fireplace, & gourmet kitchen, vacation rental in Middlebury

Mountainview mansion with patio, balcony, wood fireplace, & gourmet kitchen

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mountain Views Ski on/off Sugarbush Home - South Village, vacation rental in Middlebury

Mountain Views Ski on/off Sugarbush Home - South Village

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Steps away from tranquil Lake Champlain, vacation rental in Middlebury

Steps away from tranquil Lake Champlain

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Beautiful 1 Bedroom  Overlooking Bread Loaf Campus, vacation rental in Middlebury

Beautiful 1 Bedroom Overlooking Bread Loaf Campus

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Comfortable home w/ free WiFi - next to ski resorts, hiking trails, & lakes, vacation rental in Middlebury

Comfortable home w/ free WiFi - next to ski resorts, hiking trails, & lakes

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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