
Vacation rentals with a patio in Middletown
Find and book unique accommodations with an outdoor patio on Airbnb
Top-rated accommodations with an outdoor patio in Middletown
Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.

Lakefront Cozy - SwimSpa, Firepit, Ski 20 min away
Discover a charming 1080 sqft lakefront cottage offering modern comfort and tranquility. Wake up to peaceful Lake Garda waterfront views while staying near Farmington Valley’s conveniences. This newly remodeled retreat features a large jetted swim spa, stone patio with fire pit and grill, and direct lake access for kayaking or pedal boating perfect for relaxation. Enjoy a private getaway with nature’s beauty at your doorstep, all while being minutes from dining, shopping, and outdoor adventures.

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton
Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Breathtaking home with unforgettable views & pool!
This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or stargazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. Please let us know before booking more than 4 people whether it is just for the day or night or both. No loud music no parties.

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Bright & Private WHOLE HOUSE 4 YOU Near Everything
Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

Enchanted Cottage on the Marsh, walk to beach
Enjoy an idyllic stay at Enchanted Cottage on the Marsh! Private, quiet one bedroom cottage on Farm River with breathtaking views from deck. Take in the herons, ospreys and other birds among the natural surroundings while relaxing on your very private deck. Or take a stroll to the neighborhood beach, trails or a restaurant. Enjoy daily retreat from everyday life. We want you to have a relaxing stay with us, free from worry. 10 min walk to beach, trails, 10 min drive to Yale University.

Amazing 2BR Riverfront Gem
Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Cozy Historic Home Guest Suite
Escape to a bright, cozy guest suite next to a historic New England home! Enter through your own doorway and feel welcomed by rich dark‑wood accents and sunlight‑filled rooms. Enjoy a front yard patio, expansive yard, century‑old trees, then local cafés and a state park within a 8 minute drive or an easy day trip by train to Manhattan or Boston. Return to hominess, and modern comforts—Wi‑Fi, kitchenette, queen bed, plus the perk of free private parking. Relax and feel at home.

Entire place to yourself Cromwell/Middletown Line
Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kitchen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
Located in charming downtown Chester, our loft rests above the newly established Village Bistro; with the loft being situated above our restaurant and on Main Street please keep in mind that you may hear some background noise during normal business hours. Additionally, you will be staying in a 200-year-old structure so there is some quirkiness that goes along with an aged building such as ours but rest assured you will feel right at home in this cozy, warm, historic space.

Quiet Comfy Getaway 3 BDR home
Our newly renovated 3-bedroom home offers a comfortable and convenient stay. Perfectly located with easy access to the grocery stores, strip malls, hospitals, and parks, it's an ideal base for your trip. Our home comes with ample parking, pristine kitchen and bathrooms, mini coffee bar, cooking utensils, free WiFi, and a washer/dryer. Stay productive with our dedicated workspace and unwind in our spacious bedrooms. Book now for a home away from home experience!

The Winchester House at Science Park-Yale
Located 2 blocks from Yale University's Franklin and Murray College and Ingall's Ice rink, The Winchester House at Science Park is a newly renovated luxuriously appointed 2 bedroom 2.5 bathroom apartment. The apartment features bespoke amenities, free secure off-street parking, snacks and beverages, stylish furniture, 1000 ct. beddings, ample cooking pantry items and everything you need as a guest. Let us welcome you in relaxed luxury!
Popular amenities for Middletown accommodations with an outdoor patio
Apartment rentals with a patio

The Boathouse, private downtown Harborside suite

The Brick: Rooftop Deck Home. Walk to Yale!

Lakefront Luxury on Pattagansett

Sunny Fairfield Studio Apartment

The Millhouse Downtown Chester

Retreat in New Haven by Stephanie and Damian

The Pond Mill Retreat w/ 2 Bdrms & Pool

Sage Haven: Comfy, Family Friendly, Close to Yale
House rentals with an outdoor patio

15 acres! * Pine Pond at Devils Hopyard State Park

Charming Cape Home, Close to All

Grammy's Lake House on Lake Pocotopaug

Westshore Luxury

Cozy Cottage with Fire Pit, near Beach

Charming River Home

Spacious 3 Bedroom Ranch With Office

Lakeside Paradise with Breathtaking Sunsets
Condo rentals with a patio

Meadow View

Spacious Condo • Quick Drive to Everything

Comfortable Relaxing Ideal Oasis

Historic Estate Studio Loft

Luxury furnished condo. Attached garage. Fireplace

Seashore getaway - CT shoreline

Apartments Downtown Hartford
When is the best time to visit Middletown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $186 CAD | $184 CAD | $187 CAD | $220 CAD | $211 CAD | $200 CAD | $204 CAD | $220 CAD | $184 CAD | $184 CAD | $171 CAD | $179 CAD |
| Avg. temp | -3 °C | -1 °C | 3 °C | 10 °C | 16 °C | 20 °C | 24 °C | 23 °C | 18 °C | 12 °C | 6 °C | 0 °C |
Quick stats about vacation rentals with a patio in Middletown

Total vacation rentals
Explore 50 vacation rentals in Middletown

Nightly prices starting at
Middletown vacation rentals start at $55 CAD per night before taxes and fees

Verified guest reviews
Over 4,900 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Middletown vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middletown rentals

4.9 Average rating
Middletown stays are highly rated by guests—averaging 4.9 out of 5!
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- Beach
- Yale University
- Six Flags New England
- Cooper's Beach, Southampton
- Thunder Ridge Ski Area
- Fairfield Beach
- Ocean Beach Park
- Mohegan Sun
- Mystic Seaport Museum
- Foxwoods Resort Casino
- Kent Falls State Park
- Hammonasset Beach State Park
- Mohawk Mountain Ski Area
- Sleeping Giant State Park
- Powder Ridge Mountain Park & Resort
- Yale University Art Gallery
- Long Island Aquarium
- Amagansett Beach
- Sherwood Island State Park
- Orient Beach State Park
- Compo Beach
- Ski Sundown
- Ocean Beach
- Mount Southington Ski Area





