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Middlebury Holiday Rentals

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Check prices for these dates

In two weeks
26 Sept - 28 Sept
In one month
10 Oct - 12 Oct
In two months
7 Nov - 9 Nov
In three months
5 Dec - 7 Dec

Holiday Rentals in Middlebury

Our top choices for Middlebury holiday rentals

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Outdoor dining

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

9.4 out of 10, Exceptional, (29)
"Stayed here to visit family and it was perfect for what we needed. Would recommend staying here. "
Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed
Luxury Furnished Apartments by Hyatus Downtown at Yale
In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (54)
"Loved the property and we will surely be coming back."
Luxury Furnished Apartments by Hyatus Downtown at Yale
Charming Studio| Near Yale| Downtown New Haven
Exterior

Charming Studio| Near Yale| Downtown New Haven

10.0 out of 10, Exceptional, (3)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is HK$881
HK$1,708 total
includes taxes & fees
10 Sept - 11 Sept
Charming Studio| Near Yale| Downtown New Haven
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Dining

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Outdoor dining

Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

8.8 out of 10, Excellent, (22)
"We were very happy with the accommodations. The cottage was neat, clean and well kept, as was the property. All the amenities were as described. We had a great weekend and would highly recommend this lake house."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
Games room

Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room

2.0 out of 10, (1)
"Host never emailed info. After numerous attempts to contact them, we gave up and stayed in a hotel. VRBO gave full refund. I don’t recommend this host, but VRBO was great!"
The price is HK$1,193
HK$2,355 total
includes taxes & fees
9 Sept - 10 Sept
Cozy 1-bedroom apartment in cool New Haven with WiFi, fitness room
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.6 out of 10, Exceptional, (14)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is HK$1,790
HK$4,046 total
includes taxes & fees
10 Sept - 11 Sept
McAngel Haven: 5 mins from Yale
Cozy Country Cottage
Smart TV, fireplace

Cozy Country Cottage

2.0 star property
9.0 out of 10, Wonderful, (7)
"Very accommodating and understanding host.They are warm and willing to listen and make your stay as comfortable as possible. Trent and his family will go out of their way to make the stay memorable.. I would highly recommend the stay at this accommodation to everyone. A home away from home."
The price is HK$1,162
HK$2,048 total
includes taxes & fees
14 Sept - 15 Sept
Cozy Country Cottage
Yale Casa Verde Studio
Fridge, microwave, oven, stovetop

Yale Casa Verde Studio

10.0 out of 10, Exceptional, (4)
"Had a great stay!"
The price is HK$772
HK$1,627 total
includes taxes & fees
16 Sept - 17 Sept
Yale Casa Verde Studio
Angelica’s safe haven @ west haven
Exterior

Angelica’s safe haven @ west haven

10.0 out of 10, Exceptional, (4)
"This place was perfect for our weekend trip to New Haven. Angelica was a great Host, and communicated timely and clear. I would stay again if I ever come back to New Haven. "
The price is HK$1,068
HK$2,630 total
includes taxes & fees
9 Sept - 10 Sept
Angelica’s safe haven @ west haven
Waterfront Family Retreat on Candlewood Lake
Outdoor dining

Waterfront Family Retreat on Candlewood Lake

10.0 out of 10, Exceptional, (46)
"Wonderful! Elizabeth and John made everything seamless and enjoyable. Terrific location! "
The price is HK$6,400
HK$11,520 total
includes taxes & fees
10 Sept - 11 Sept
Waterfront Family Retreat on Candlewood Lake
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (47)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Dining

Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT

10.0 out of 10, Exceptional, (13)
"Beautiful location and lots of space for a large group. This rental is really about the outdoor space and activities. Would love to return!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Lakeview Estate - Chef's Kitchen - NYC Getaway
Property grounds

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (30)
"Beautiful, spacious property with all the amenities we needed and more. I would recommend and we will certainly return!"
Lakeview Estate - Chef's Kitchen - NYC Getaway
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Exterior

Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable

10.0 out of 10, Exceptional, (3)
"Perfect for families."
The price is HK$1,209
HK$3,016 total
includes taxes & fees
10 Sept - 11 Sept
Green N' Groovy in the Heart of East Rock Near DT | Yale |Cozy N' Comfortable
Family Gem on Dyer Street
Dining

Family Gem on Dyer Street

The price is HK$3,453
HK$7,480 total
includes taxes & fees
14 Sept - 15 Sept
Family Gem on Dyer Street
Modern Beach Home - Waterview, close to restaurants, universities and hospitals
Beach

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (3)
"Great stay at this lovely house. Walk to beach! Perfect backyard to enjoy a beautiful weekend "
Modern Beach Home - Waterview, close to restaurants, universities and hospitals
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Dining

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (23)
"We love being there do we extended our stay. Would have liked to stay even longer. Very relaxing and peaceful."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Luxurious 3BR Apartment with Premium Amenities
Smart TV, video games, ping pong, books

Luxurious 3BR Apartment with Premium Amenities

10.0 out of 10, Exceptional, (16)
"The property was great- amenities like linens, decor, kitchen items were high quality. Great view also!"
Luxurious 3BR Apartment with Premium Amenities
Amazing Lakefront Property
Interior

Amazing Lakefront Property

9.8 out of 10, Exceptional, (26)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
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.
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Top Middlebury Hotel Reviews

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

10/10 Excellent
"Carpet in the hallways needs to be cleaned. Very dirty"
Claudine 4-night trip
Posted 7 days ago
Holiday Inn Express Southington by IHG

Find out more about Middlebury

Find out more about Middlebury

Search for holiday rentals in Middlebury on Expedia! You can easily find your home rentals, villas, holiday apartments in Middlebury using one of the methods below:

  • View our selection of featured holiday rentals in Middlebury
  • Use the map to find apartments and other holiday homes in the Middlebury neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middlebury while they last

Look no further and take a look at our great range of rental properties in Middlebury!

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Frequently asked questions

Can I find holiday rentals in Middlebury?

Yes, there are holiday rentals in Middlebury close to Quassy Amusement Park, or you can select a more secluded option if you're looking for a relaxing stay. Middlebury is known for its parks.

What are some of the best holiday rentals that Middlebury has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This holiday home rental outside of Middlebury offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What’s there to see and do in Middlebury?

Family-friendly attractions include Quassy Amusement Park, whereas Lake Quassapaug is a spot to enjoy the outdoors. In the wider area, you’ll find Waterbury City Hall and Palace Theatre.

What’s a holiday rental in Middlebury like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a family trip.