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Middlebury Holiday Rentals

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50 rentals in Middlebury.
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Walk everywhere in Middlebury, holiday rental in Middlebury
Walk everywhere in Middlebury, holiday rental in Middlebury
Walk everywhere in Middlebury, holiday rental in Middlebury

Walk everywhere in Middlebury

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Cottage within walking distance of Middlebury College/canoe available, holiday rental in Middlebury
Charming Cottage within walking distance of Middlebury College/canoe available, holiday rental in Middlebury
Charming Cottage within walking distance of Middlebury College/canoe available, holiday rental in Middlebury

Charming Cottage within walking distance of Middlebury College/canoe available

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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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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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 9
Match: Sleeps
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Sunny, beautiful, & quiet home on 27 acres with mountain views, holiday rental in Middlebury
Sunny, beautiful, & quiet home on 27 acres with mountain views, holiday rental in Middlebury
Sunny, beautiful, & quiet home on 27 acres with mountain views, holiday rental in Middlebury

Sunny, beautiful, & quiet home on 27 acres with mountain views

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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Breathtaking New Lake Champlain Beach,Foliage,Romantic,Ski & Spring Escape!, holiday rental in Middlebury
Breathtaking New Lake Champlain Beach,Foliage,Romantic,Ski & Spring Escape!, holiday rental in Middlebury
Breathtaking New Lake Champlain Beach,Foliage,Romantic,Ski & Spring Escape!, holiday rental in Middlebury

Breathtaking New Lake Champlain Beach,Foliage,Romantic,Ski & Spring Escape!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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Classic Vermont Cabin On 2.5 Acres With Lake Frontage, holiday rental in Middlebury
Classic Vermont Cabin On 2.5 Acres With Lake Frontage, holiday rental in Middlebury
Classic Vermont Cabin On 2.5 Acres With Lake Frontage, holiday rental in Middlebury

Classic Vermont Cabin On 2.5 Acres With Lake Frontage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded, Safe, fun - All to yourselves Campfires! Hot Tub, Fireplace, Game Rm, holiday rental in Middlebury
Secluded, Safe, fun - All to yourselves Campfires! Hot Tub, Fireplace, Game Rm, holiday rental in Middlebury
Secluded, Safe, fun - All to yourselves Campfires! Hot Tub, Fireplace, Game Rm, holiday rental in Middlebury

Secluded, Safe, fun - All to yourselves Campfires! Hot Tub, Fireplace, Game Rm

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Lake Front Home with Stunning Views, holiday rental in Middlebury
Lake Front Home with Stunning Views, holiday rental in Middlebury
Lake Front Home with Stunning Views, holiday rental in Middlebury

Lake Front Home with Stunning Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lake Front Quiet Cottage, holiday rental in Middlebury
Lake Front Quiet Cottage, holiday rental in Middlebury
Lake Front Quiet Cottage, holiday rental in Middlebury

Lake Front Quiet Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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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
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Spacious 4-season Lake Champlain charming contemporary house, holiday rental in Middlebury
Spacious 4-season Lake Champlain charming contemporary house, holiday rental in Middlebury
Spacious 4-season Lake Champlain charming contemporary house, holiday rental in Middlebury

Spacious 4-season Lake Champlain charming contemporary house

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Waterfront Guest House, holiday rental in Middlebury
Waterfront Guest House, holiday rental in Middlebury
Waterfront Guest House, holiday rental in Middlebury

Waterfront Guest House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Breathtaking New Lake Champlain Beach,Ski Escape!, holiday rental in Middlebury
Breathtaking New Lake Champlain Beach,Ski Escape!, holiday rental in Middlebury
Breathtaking New Lake Champlain Beach,Ski Escape!, holiday rental in Middlebury

Breathtaking New Lake Champlain Beach,Ski Escape!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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VT VACATION PARADISE - Lake Champlain Perfect 4 LG GROUPS/ 3 cottages Available!, holiday rental in Middlebury
VT VACATION PARADISE - Lake Champlain Perfect 4 LG GROUPS/ 3 cottages Available!, holiday rental in Middlebury
VT VACATION PARADISE - Lake Champlain Perfect 4 LG GROUPS/ 3 cottages Available!, holiday rental in Middlebury

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!, holiday rental in Middlebury
Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!, holiday rental in Middlebury
Private Ski Lodge with Giant Hot Tub Less Than Two Miles to Sugarbush!, holiday rental in Middlebury

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

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

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Elmtucket, a charming year round home on the shores of Lake Champlain, holiday rental in Middlebury
Elmtucket, a charming year round home on the shores of Lake Champlain, holiday rental in Middlebury
Elmtucket, a charming year round home on the shores of Lake Champlain, holiday rental in Middlebury

Elmtucket, a charming year round home on the shores of Lake Champlain

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Lakefront Views, cozy, clean, book filled, holiday rental in Middlebury
Lakefront Views, cozy, clean, book filled, holiday rental in Middlebury
Lakefront Views, cozy, clean, book filled, holiday rental in Middlebury

Lakefront Views, cozy, clean, book filled

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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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
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An Idyllic Vermont Experience Minutes from Middlebury College!, holiday rental in Middlebury
An Idyllic Vermont Experience Minutes from Middlebury College!, holiday rental in Middlebury
An Idyllic Vermont Experience Minutes from Middlebury College!, holiday rental in Middlebury

An Idyllic Vermont Experience Minutes from Middlebury College!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded house w/mountain views mins to Middlebury, flex cancellation policy, holiday rental in Middlebury
Secluded house w/mountain views mins to Middlebury, flex cancellation policy, holiday rental in Middlebury
Secluded house w/mountain views mins to Middlebury, flex cancellation policy, holiday rental in Middlebury

Secluded house w/mountain views mins to Middlebury, flex cancellation policy

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Classic log cabin on a pond w/ mountain views, deck & pool table - dogs OK!, holiday rental in Middlebury
Classic log cabin on a pond w/ mountain views, deck & pool table - dogs OK!, holiday rental in Middlebury
Classic log cabin on a pond w/ mountain views, deck & pool table - dogs OK!, holiday rental in Middlebury

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

Holiday Rental House
3 bedrooms
3 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
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Lake Champlain Vacation Home - Summer Avalability: Dock, Decks & Private Beach, holiday rental in Middlebury
Lake Champlain Vacation Home - Summer Avalability: Dock, Decks & Private Beach, holiday rental in Middlebury
Lake Champlain Vacation Home - Summer Avalability: Dock, Decks & Private Beach, holiday rental in Middlebury

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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
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Park Model Rental in Campground., holiday rental in Middlebury
Park Model Rental in Campground., holiday rental in Middlebury
Park Model Rental in Campground., holiday rental in Middlebury

Park Model Rental in Campground.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Little City 'Big Heart', holiday rental in Middlebury
Little City 'Big Heart', holiday rental in Middlebury
Little City 'Big Heart', holiday rental in Middlebury

Little City 'Big Heart'

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Cottage * Waterhouses, holiday rental in Middlebury
Cottage * Waterhouses, holiday rental in Middlebury
Cottage * Waterhouses, holiday rental in Middlebury

Cottage * Waterhouses

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW to VRBO! Stunning 3 Bedroom Lake House/SkiHouse!, holiday rental in Middlebury
NEW to VRBO! Stunning 3 Bedroom Lake House/SkiHouse!, holiday rental in Middlebury
NEW to VRBO! Stunning 3 Bedroom Lake House/SkiHouse!, holiday rental in Middlebury

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Escape to an Historic Lodge with Lake Dunmore at your feet!, holiday rental in Middlebury
Escape to an Historic Lodge with Lake Dunmore at your feet!, holiday rental in Middlebury
Escape to an Historic Lodge with Lake Dunmore at your feet!, holiday rental in Middlebury

Escape to an Historic Lodge with Lake Dunmore at your feet!

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace, holiday rental in Middlebury
Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace, holiday rental in Middlebury
Beautiful, rustic home w/ on-site playground, deck, patio, grill, and fireplace, holiday rental in Middlebury

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
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Lake Champlain Waterfront House with Private Dock and Boat Mooring, holiday rental in Middlebury
Lake Champlain Waterfront House with Private Dock and Boat Mooring, holiday rental in Middlebury
Lake Champlain Waterfront House with Private Dock and Boat Mooring, holiday rental in Middlebury

Lake Champlain Waterfront House with Private Dock and Boat Mooring

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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1888 3 story Farmhouse w/ great views 15 min. from Midd campus, holiday rental in Middlebury
1888 3 story Farmhouse w/ great views 15 min. from Midd campus, holiday rental in Middlebury
1888 3 story Farmhouse w/ great views 15 min. from Midd campus, holiday rental in Middlebury

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Quiet Camp on the lake “Relax, Refresh, Unwind “, holiday rental in Middlebury
Quiet Camp on the lake “Relax, Refresh, Unwind “, holiday rental in Middlebury
Quiet Camp on the lake “Relax, Refresh, Unwind “, holiday rental in Middlebury

Quiet Camp on the lake “Relax, Refresh, Unwind “

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
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Beauty, Comfort  & Quality - 4 Bedroom Home in the Midst of Vermont's Splendor, holiday rental in Middlebury
Beauty, Comfort  & Quality - 4 Bedroom Home in the Midst of Vermont's Splendor, holiday rental in Middlebury
Beauty, Comfort  & Quality - 4 Bedroom Home in the Midst of Vermont's Splendor, holiday rental in Middlebury

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Cozy Mountain Yurt on Organic Farm, holiday rental in Middlebury
Cozy Mountain Yurt on Organic Farm, holiday rental in Middlebury
Cozy Mountain Yurt on Organic Farm, holiday rental in Middlebury

Cozy Mountain Yurt on Organic Farm

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

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Listing On Lake Dunmore, holiday rental in Middlebury
New Listing On Lake Dunmore, holiday rental in Middlebury
New Listing On Lake Dunmore, holiday rental in Middlebury

New Listing On Lake Dunmore

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Far Enough, An Old World Vermont Estate, holiday rental in Middlebury
Far Enough, An Old World Vermont Estate, holiday rental in Middlebury
Far Enough, An Old World Vermont Estate, holiday rental in Middlebury

Far Enough, An Old World Vermont Estate

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Quiet Non-Smoking Lakefront Home on Lake Champlain, holiday rental in Middlebury
Quiet Non-Smoking Lakefront Home on Lake Champlain, holiday rental in Middlebury
Quiet Non-Smoking Lakefront Home on Lake Champlain, holiday rental in Middlebury

Quiet Non-Smoking Lakefront Home on Lake Champlain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Escape to Quiet Fern Lake, 15 Minutes from Middlebury, holiday rental in Middlebury
Escape to Quiet Fern Lake, 15 Minutes from Middlebury, holiday rental in Middlebury
Escape to Quiet Fern Lake, 15 Minutes from Middlebury, holiday rental in Middlebury

Escape to Quiet Fern Lake, 15 Minutes from Middlebury

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy Cottage overlooking Lake Dunmore, holiday rental in Middlebury
Cozy Cottage overlooking Lake Dunmore, holiday rental in Middlebury
Cozy Cottage overlooking Lake Dunmore, holiday rental in Middlebury

Cozy Cottage overlooking Lake Dunmore

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Beautiful 1 Bedroom  Overlooking Bread Loaf Campus, holiday rental in Middlebury
Beautiful 1 Bedroom  Overlooking Bread Loaf Campus, holiday rental in Middlebury
Beautiful 1 Bedroom  Overlooking Bread Loaf Campus, holiday rental in Middlebury

Beautiful 1 Bedroom Overlooking Bread Loaf Campus

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The Groovy Lake House, holiday rental in Middlebury
The Groovy Lake House, holiday rental in Middlebury
The Groovy Lake House, holiday rental in Middlebury

The Groovy Lake House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake & Mountain Chalet, holiday rental in Middlebury
Lake & Mountain Chalet, holiday rental in Middlebury
Lake & Mountain Chalet, holiday rental in Middlebury

Lake & Mountain Chalet

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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