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Vacation Homes in Middlebury

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

9.0 out of 10, Wonderful, (16)
"We really enjoyed our stay. The house is walking distance from the lake and a good break for anyone trying to escape the bustle of NYC. The house was very clean and we felt safe and comfortable here’s the outdoor fire pit was a very nice touch."
Lakehouse, Boat Dock, Kayaks, Fire-Pit, King Bed, 1 Hour & 15 Min from NYC etc!

Cozy Lakefront Bungalow w firepit/dock/kayaks

10.0 out of 10, Exceptional, (29)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks

Tranquil Litchfield Connecticut Retreat".

9.2 out of 10, Wonderful, (14)
"My friends and stayed for a night. The house is nice and the owners is very communicative. "
The price is AED 826
AED 1,174 total
includes taxes & fees
4 Aug - 5 Aug
Tranquil Litchfield Connecticut Retreat".

Private Annex/Former Artist Studio

10.0 out of 10, Exceptional, (51)
"We had a wonderful 3 night stay in the Artist Annex! Everyrhing was jus"
Private Annex/Former Artist Studio

Updated ranch Home 4 minutes from the beach on a quiet end street.

8.4 out of 10, Very Good, (7)
"It was everything that I expected. Fabian was very attentive and responsive. I would definitely rent again. "
Updated ranch Home 4 minutes from the beach on a quiet end street.

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

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Cozy 3 bedroom minutes from Yale and the beach

8.0 out of 10, Very Good, (1)
"Would recommend. It was quaint second story apartment in an older home. Nicely updated."
Cozy 3 bedroom minutes from Yale and the beach

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (25)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Spacious Woodbury Home w/ Pool + Hot Tub!

8.0 out of 10, Very Good, (3)
"Great spot and location, house was clean and enjoyable. Pool needs additional care and cleaning "
Spacious Woodbury Home w/ Pool + Hot Tub!

Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

10.0 out of 10, Exceptional, (3)
"I stayed with my mom and the 2 bedroom 1 bath was perfect for our stay. The house way cozy and in a quiet area. Would absolutely stay again; my mom is already talking about coming back to explore more of the surrounding areas!"
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (27)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

Private Apartment in Berlin

2.0 star property
10.0 out of 10, Exceptional, (4)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
The price is AED 520
AED 1,554 total
includes taxes & fees
11 Aug - 12 Aug
Private Apartment in Berlin

NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

10.0 out of 10, Exceptional, (9)
"We had a wonderful vacation with our grandchildren and family. The children lived in the water if not kayaking or water boards they were fishing!! Rainy days puzzles were our entertainment the summer house provided everything one wanted or needed. It was a very delightful vacation"
NEW Candlewood Lake 4BR 2BA Direct Waterfront Home Dock~Fire Pit~Winter Special!

Litchfield County Getaway

10.0 out of 10, Exceptional, (43)
"Property is a great getaway from a fast paced life. Quiet and beautiful. Open floor concept. Country living with all the update of the city. Very clean. "
Litchfield County Getaway

Private hidden gem walking distance to town, restaurants, and shopping!

9.8 out of 10, Exceptional, (18)
"Great property!"
Private hidden gem walking distance to town, restaurants, and shopping!

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (12)
"The house was as advertised and located in a really quiet neighborhood. The host was easy to work with and responded to me each time I texted her. If the opportunity ever comes up again, we would definitely stay at this property again."
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

2.0 star property
10.0 out of 10, Exceptional, (7)
"We met our kids (who live on the east coast) at Natures Nest and really enjoyed our time here. We cooked 2 big meals and the kitchen had everything we needed…even spices & coffee. And Marco left some apples, sweets and wine for us! He was very responsive and helpful anytime we had questions, and gave us great recommendations. Everything was great!"
Nature's Nest - Indoor/Outdoor Forest Retreat; Fire Pit; Fireplace; onsite Brook

Westshore Luxury

7.0 out of 10, Good, (4)
"Perfect location near the beach! When we stayed the weather wasn’t ideal for the beach day but I can only imagine how perfect this house would be in a beautiful day! The host had a wagon and beach toys available as well which was wonderful. Very cute property. I was unsure of our check out instructions other than to ensure we cleaned our dishes and messaged the host and never heard back but other than that our stay was great. "
The price is AED 1,833
AED 2,503 total
includes taxes & fees
28 Jul - 29 Jul
Westshore Luxury

Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

10.0 out of 10, Exceptional, (3)
"Home was very nice and as described. Perfect for our needs "
Spacious 5-bedroom house in lake community, fireplace, hot tub, washer/dryer

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub

Colonial steps from beach: 3BR, 2BA Oasis with Hot Tub
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