Search Vacation Homes in Middlebury

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 231 Vacation Homes in Middlebury with updated reviews, rates, and availability.

Pristene lakefront property - charming, quiet, and rustic for nature lovers.
Breathtaking sunsets on Cedar Lake

Pristene lakefront property - charming, quiet, and rustic for nature lovers.

8.0 out of 10, Very Good, (71)
"Plenty of room for the whole family."
Pristene lakefront property - charming, quiet, and rustic for nature lovers.
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
Beach

Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!

10.0 out of 10, Exceptional, (175)
"Absolutely perfect location for what we were looking for! Beautiful view of the Lake Champlain and the house was perfect and comfortable- it had everything we needed! Peaceful and relaxing right before Christmas. "
Breathtaking New Premier Lake Champlain Waterfront Beach,Foliage,Ski Escape!
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
Mountain Views from the minute you drive in to the house

6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill

10.0 out of 10, Exceptional, (22)
"Our family stayed at Evan's home because we were attending a wedding (conveniently up the road) at Mountain Top Resort. The home gushes with Vermont charm! It was beautifully and thoughtfully decorated which made our stay so cozy. Evan thought of everything- from exact GPS directions, to helpful notes around the home to help his guests be comfortable! Evan was very helpful at every stage of our stay! We would absolutely 100% recommend staying at Evan's beautiful home!"
6 Minute Walk to Mountain Top Inn 4 BR, Sleeps 9-10, Pet Friendly, Views & Grill
NEW! Modern Log Cabin with Skiing & Work-Friendly Setup
"Tree","Architecture","Building","Outdoors","Shelter"

NEW! Modern Log Cabin with Skiing & Work-Friendly Setup

NEW! Modern Log Cabin with Skiing & Work-Friendly Setup
Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.
Upper Deck View from Master Suite

Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.

9.2 out of 10, Wonderful, (114)
"Amazing "
Majestic 4 Season Lake Champlain House - 350K make over - Private Beach & Dock.
The Brandon Inn - Fourth Floor Queen Room
Point of interest

The Brandon Inn - Fourth Floor Queen Room

8.4 out of 10, Very Good, (5)
"Clean, great location…restaurants, quaint interesting little shops… rent a vehicle and go hiking explore etc"
The price is SAR 544
SAR 693 total
includes taxes & fees
26 Jan - 27 Jan
The Brandon Inn - Fourth Floor Queen Room
Middlebury Gem open concept and 5 minutes from town
Exterior detail

Middlebury Gem open concept and 5 minutes from town

10.0 out of 10, Exceptional, (70)
"House is a perfect option for families visiting Middlebury College. Spacious, clean, and well appointed!"
Middlebury Gem open concept and 5 minutes from town
Beautiful lake house on Lake Champlain!
Exterior

Beautiful lake house on Lake Champlain!

9.8 out of 10, Exceptional, (95)
"Beautiful lake views on this lakefront property. Clean, well appointed and great communication with property manager. Would definitely return- thank you for a lovely visit!"
Beautiful lake house on Lake Champlain!
Historic home on 1 acre with snowmobile trails in backyard & mountain views

Historic home on 1 acre with snowmobile trails in backyard & mountain views

9.8 out of 10, Exceptional, (18)
"My husband and I enjoyed our stay with beautiful views and off the beaten path. We were comfortable in the space and looked forward to coming back each evening after a day of exploring. Wifi worked well. Host left a helpful binder with information and recommendations. We used the kitchen, and it had the cookware we needed."
Historic home on 1 acre with snowmobile trails in backyard & mountain views
Dog-friendly, three-story home with fireplace and washer/dryer - near Sugarbush

Dog-friendly, three-story home with fireplace and washer/dryer - near Sugarbush

9.8 out of 10, Exceptional, (7)
"Great house with beautiful scenery! We loved this stay"
Dog-friendly, three-story home with fireplace and washer/dryer - near Sugarbush
Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak
Relax by the fireplace after a fun day on the mountain

Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak

Ski-in and Ski-out at Sugarbush Resort at Lincoln Peak
Top of the Hill Modern Retreat
Front of House

Top of the Hill Modern Retreat

10.0 out of 10, Exceptional, (1)
"I love this place! New and spacious. The kitchen has everything you need for the stay. My wife loves cooking in there. The only complaint is the water pressure is too weak. It is definite worth for families who love to cook."
The price is SAR 583
SAR 2,154 total
includes taxes & fees
27 Jan - 28 Jan
Top of the Hill Modern Retreat
Moose Lodge - Rustic and Cozy
Exterior

Moose Lodge - Rustic and Cozy

9.8 out of 10, Exceptional, (49)
"The property was great. The neighbors that we were lucky enough to meet are very nice. The house was clean and very well maintained. I definitely would rent from Nicholas again. "
Moose Lodge - Rustic and Cozy
Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (114)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym
Ellen’s Edge Winter Wonderland

Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym

10.0 out of 10, Exceptional, (4)
"Such a great house! Perfect location, wonderful amenities and fabulous host! Couldn’t have asked for a better home for our October weekend! Will definitely be back!"
Ellen’s Edge~ Game Room~Home Theater~Hot Tub~Home Gym
Light-filled retreat in Mad River Valley with internet & deck

Light-filled retreat in Mad River Valley with internet & deck

10.0 out of 10, Exceptional, (2)
"This home is the perfect place to escape the busy lifestyle of every day life. To relax and reset."
The price is SAR 758
SAR 2,254 total
includes taxes & fees
26 Jan - 27 Jan
Light-filled retreat in Mad River Valley with internet & deck
Hague Vacation Rental ~ 2 Mi to Lake George!
Hague Vacation Rental | 2BR | 1.5BA | 864 Sq Ft | Stairs Required

Hague Vacation Rental ~ 2 Mi to Lake George!

7.2 out of 10, Good, (5)
"Located conveniently close to Rogers Rock State Park with boat inspection station and launch. This is a no-frills property which was quiet and clean, providing a pleasant stay. The driveway is steep and somewhat tight, but I was able to park a Ram pickup with 8ft bed and boat trailer without much trouble. I enjoyed the lack of cell service and WiFi - it was GREAT. It did smell somewhat like pets upon first entering, as it was a very humid day. we moved the dog bed downstairs and aired the...
Hague Vacation Rental ~ 2 Mi to Lake George!
4 Mi to Sugarbush Resort: Waitsfield Retreat
Waitsfield Vacation Rental | 4BR | 3BA | 2,800 Sq Ft | Stairs Required

4 Mi to Sugarbush Resort: Waitsfield Retreat

9.2 out of 10, Wonderful, (47)
"The location of the house was good for Bolton Valley, and Stowe and great for Sugarbush. The house has all you need for entertainment, comfort and amenities. We especially liked the fast drip, commercial coffee maker! The hot tub was also a hit after skiing each day. Good communication, well maintained and plenty of room. "
4 Mi to Sugarbush Resort: Waitsfield Retreat
Killington Vermont Ski and Snowmobiling House
Outside view

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
Lake Champlain Estate. 25 Acres, 1500 Feet Lakefront, Beautiful View.
View from Lake Champlain

Lake Champlain Estate. 25 Acres, 1500 Feet Lakefront, Beautiful View.

Lake Champlain Estate. 25 Acres, 1500 Feet Lakefront, Beautiful View.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Middlebury
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Middlebury

Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub
Ultimate relaxing vacation
Breathtaking , relaxing and private haven. Perfect for unwinding from busy life

Ultimate relaxing vacation

9.8 out of 10, Exceptional, (181)
"We all had a wonderful time, enjoying this cozy, homey cabin, and the fantastic view over Perch Pond. We were comfortable inside, and took many walks outside... beautiful!"
The price is SAR 525
SAR 672 total
includes taxes & fees
27 Jan - 28 Jan
Ultimate relaxing vacation
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.