Search Vacation Homes in Middlebury

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Middlebury vacation homes

Private kitchen

Cozy Room in charming New Haven near Yale/Hospitals!

Cozy Room in charming New Haven near Yale/Hospitals!
The Hill
9.4 out of 10, Exceptional, (3 reviews)
"Very nice house and very clean I really love it "
United States
Peterson
The price is AED 264
AED 568 total
includes taxes & fees
18 Apr - 19 Apr
Cozy Room in charming New Haven near Yale/Hospitals!
Marina

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.

Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Fair Haven
9.6 out of 10, Exceptional, (15 reviews)
"A cozy pet and family-friendly property. Very spacious."
United States
Wallace R.
The price is AED 735
AED 1,304 total
includes taxes & fees
20 Apr - 21 Apr
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
1 bedroom, iron/ironing board, WiFi, bed sheets

Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AED 433
AED 1,071 total
includes taxes & fees
1 May - 2 May
Once the old Schools house now a newly furnished Apartment
Marina

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.

Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Fair Haven
7.6 out of 10, Good, (5 reviews)
"Thanks for hosting us! It was clean and nice. For future guests, a long body mirror might be nice but we had a wonderful time and appreciated you bringing us extra towels quickly!"
United States
Jamie S.
The price is AED 514
AED 940 total
includes taxes & fees
21 Apr - 22 Apr
Gorgeous Waterfront 2 Bedroom 1 Bath Modern Home.
Dining

Stocked home close to Yale, in Heart of New Haven

Stocked home close to Yale, in Heart of New Haven
Mill River
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is AED 463
AED 813 total
includes taxes & fees
20 Apr - 21 Apr
Stocked home close to Yale, in Heart of New Haven
Dining

McAngel Haven: 5 mins from Yale

McAngel Haven: 5 mins from Yale
West Haven
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is AED 843
AED 1,921 total
includes taxes & fees
19 Apr - 20 Apr
McAngel Haven: 5 mins from Yale
Private kitchen

Welcoming 4-bedroom house in charming Hamden

Welcoming 4-bedroom house in charming Hamden
Hamden
10.0 out of 10, Exceptional, (1 review)
"Host was kind and attentive. Location was convenient and the home was clean and spacious. "
United States
Renee H.
The price is AED 985
AED 1,728 total
includes taxes & fees
28 Apr - 29 Apr
Welcoming 4-bedroom house in charming Hamden
Interior

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
The price is AED 364
AED 492 total
includes taxes & fees
19 Apr - 20 Apr
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Fridge, microwave, oven, stovetop

#27- Luxury Collection

#27- Luxury Collection
Southington
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home, well designed and spacious rooms. Host was fantastic and communication was great! Thank you"
United States
C B.
The price is AED 762
AED 1,700 total
includes taxes & fees
29 Apr - 30 Apr
#27- Luxury Collection
Fridge, microwave, oven, stovetop

Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale
Fair Haven
9.2 out of 10, Wonderful, (23 reviews)
"This house has everything you need to enjoy a getaway. Clean, It will sleep 20 and their is room for 20 to gather."
United States
Kathy B.
The price is AED 2,162
AED 2,761 total
includes taxes & fees
4 May - 5 May
Heavenly Home in New Haven /5 mins drive from Yale
Fridge, microwave, oven, stovetop

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (3 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is AED 658
AED 2,244 total
includes taxes & fees
20 Apr - 21 Apr
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is AED 959
AED 1,461 total
includes taxes & fees
18 Apr - 19 Apr
Litchfield Retreat, Wineries, Foliage & Skiing
Exterior detail

1-bedroom vacation home 22 minutes from Quinnipiac University

1-bedroom vacation home 22 minutes from Quinnipiac University
Wolcott
9.6 out of 10, Exceptional, (4 reviews)
"Very clean and the host was great "
United States
David G.
The price is AED 551
AED 1,456 total
includes taxes & fees
30 Apr - 1 May
1-bedroom vacation home 22 minutes from Quinnipiac University
Terrace/patio

3-bedroom house just walking distance from Yale and Downtown

3-bedroom house just walking distance from Yale and Downtown
Dixwell
3-bedroom house just walking distance from Yale and Downtown
Marina

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
The price is AED 2,094
AED 3,337 total
includes taxes & fees
20 Apr - 21 Apr
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
TV, fireplace

#41- Available 12/8! - sleeps 14

#41- Available 12/8! - sleeps 14
Southington
The price is AED 1,175
AED 2,303 total
includes taxes & fees
13 May - 14 May
#41- Available 12/8! - sleeps 14
Dining

Large group haven!

Large group haven!
West New Haven
9.4 out of 10, Exceptional, (3 reviews)
"Nice property. Lots of sleeping space and accommodation for large groups. Just what we needed. The only defect is that the lighting is poor in the second floor bedrooms. "
United States
Cameron L.
The price is AED 1,833
AED 3,492 total
includes taxes & fees
23 Apr - 24 Apr
Large group haven!
TV, fireplace

Expansive New Haven Home | Near Yale University

Expansive New Haven Home | Near Yale University
West New Haven
Expansive New Haven Home | Near Yale University
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (7 reviews)
"Great spot "
United States
Mike P.
The price is AED 1,488
AED 2,605 total
includes taxes & fees
22 Apr - 23 Apr
Awesome Lake Home with tons of fun!
TV, fireplace

#30 - Spacious & Cozy!

#30 - Spacious & Cozy!
Southington
6.8 out of 10, (5 reviews)
"Perfect spot to attend a family member's wedding at Aqua Turf. The house is very interesting (in a good way) and there's so much room for everyone! We enjoyed our short stay."
United States
Sandra B.
#30 - Spacious & Cozy!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middlebury Hotel Reviews

New Haven Hotel

New Haven Hotel

6/10 Okay
"The location was excellent and all things Yale were in walking distance. However on Friday and Saturday nights there is a very loud nightclub blasting music until 2:00 am. "
Michelle 5-night trip
Posted 2 hours ago
New Haven Hotel

Explore a world of travel with Expedia