Middletown Rentals
From $171 per night (USD)VRBO
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This modern apartment is perfect for a night away from home , or a long term stay . This hidden gem is tucked away in mi ...
From $171 per night (USD)VRBO
From $62 per night (USD)Expedia
Rent A Room In This Spacious Victorian
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Rent a room in this spacious vintage Victorian style colonial. This home is located in an ideal central location, a blo ...
From $62 per night (USD)Expedia
From $700 per night (USD)VRBO
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Quoted from a renter " This property has a million dollar view!" Featured in the 2022 movie Damons Revenge https://yout ...
From $700 per night (USD)VRBO
From $216 per night (USD)Expedia
Cozy newly remodeled home close to major amenities in Connecticut a
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Clean, spacious, beautiful kitchen and bath newly remodeled closed to major stores and restaurants 46 Braeburn Ln is a ...
From $216 per night (USD)Expedia
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Little House on River - architectural gem
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy Little House designed by renowned architect offers wonderful opportunity to vacation, work from home, or simply enj ...
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From $763 per night (USD)VRBO
Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Escape to this stunning, recently restored, 5 bedroom retreat in a historic village only two hours away from NYC and Bos ...
From $763 per night (USD)VRBO
From $247 per night (USD)VRBO
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the peace of this perfect colonial 3 bedroom 2bath Hideaway that welcomes you to a bright and airy living space, c ...
From $247 per night (USD)VRBO
From $254 per night (USD)Expedia
Modern Middletown Retreat, Minutes to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Whether you’re visiting family, seeking outdoor adventure, or simply exploring a new area, this sleek 3-bedroom, 1-bathr ...
From $254 per night (USD)Expedia
From $344 per night (USD)VRBO
#24 *Serenity* A Lakefront Cottage Retreat
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Closed the month of November for some exciting new upgrades! Stunning FALL FOLIAGE & WINTER VIEWS! This Lakefront Cott ...
From $344 per night (USD)VRBO
From $253 per night (USD)Expedia
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Keep it simple at this peaceful and centrally located apartment! Completely open concept and fully renovated. Plenty of ...
From $253 per night (USD)Expedia
From $330 per night (USD)VRBO
Charming private home on the Connecticut River that comfortably sleeps 11 people
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Beautiful River Views and River Access! This unique 5 bed, 2 full bath contemporary sits on 1.39 acres of tranquil, priv ...
From $330 per night (USD)VRBO
From $59 per night (USD)Expedia
Rent A Room In This Spacious Victorian
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Rent a room in this spacious vintage Victorian style colonial. This home is located in an ideal central location, a blo ...
From $59 per night (USD)Expedia
From $55 per night (USD)VRBO
Rent A Room In A Spacious Victorian
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Rent a room in this spacious vintage Victorian style colonial. This home is located in an ideal central location, a blo ...
From $55 per night (USD)VRBO
From $1321 per night (USD)VRBO
A Luxury Estate, Elegant, Historical, Hot Tub, Salt Water Pool ~The White Lion~
- Bedrooms:
- 10
- Bathrooms:
- 9
- Sleeps:
- 16
Escape the frenzy of the world in this family friendly spacious and serene space. White Lion Manor is a gated estate loc ...
From $1321 per night (USD)VRBO
From $597 per night (USD)VRBO
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bring the whole family for fantastic vacation to this great place with lots of room to relax and unwind. Hot Tub for 5 , ...
From $597 per night (USD)VRBO
From $415 per night (USD)Expedia
Private Apt in Middletown-Wesleyan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our charming apartment located in the heart of Middletown, just a stone's throw away from Wesleyan University ...
From $415 per night (USD)Expedia
From $436 per night (USD)VRBO
#29 - Modern 5 Bedroom/2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Discover comfort and convenience in our stylish rental. 5 Bedrooms with 4 king beds & 1 queen, two living rooms with hug ...
From $436 per night (USD)VRBO
From $406 per night (USD)Expedia
#40 - Spacious, Sleek & Cozy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our warm and inviting home, ideal for guests attending weddings, visiting family, or in need of temporary hou ...
From $406 per night (USD)Expedia
From $318 per night (USD)VRBO
Charming Connecticut Hideaway
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: This beautifully remodeled two bedroom single family home is situated on a large private lot in the quaint town ...
From $318 per night (USD)VRBO
From $331 per night (USD)Expedia
Walk to Wesleyan & Dwtn - New hot tub with outdoor TV
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Don't miss this fully renovated 2nd floor family friendly 3br apt in a historic home built in 1829. Formerly owned by ...
From $331 per night (USD)Expedia
From $256 per night (USD)VRBO
Family Stays: Middletown, CT
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Centrally Located Cozy Family Vacation Home: Just 1.2 miles from Wesleyan University, our space is perfect for families, ...
From $256 per night (USD)VRBO
From $495 per night (USD)Expedia
Modern Luxury, The Perfect Getaway Awaits
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Modern Comfort Meets Convenience – Your Perfect Getaway Awaits Welcome to this stunning brand-new 3-bedroom, 3-bathroom ...
From $495 per night (USD)Expedia
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3-bedroom house in tranquil Middletown with WiFi, AC. Enjoy your stay
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the beauty of Middletown from this 3-bedroom house. The pleasant interior features 3 queen beds, a cozy living ...
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From $196 per night (USD)Expedia
Cozy Guest Suite in Historic Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Escape to a bright, cozy guest suite next to a historic New England home! Enter through your own doorway and feel welcom ...
From $196 per night (USD)Expedia
From $368 per night (USD)VRBO
Soothing 2-bedroom lower-level apartment in Berlin
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Get ready to relax in this 2-bedroom lower-level apartment in Berlin with own entrance in the rear of the house. This de ...
From $368 per night (USD)VRBO