Vacation rentals in Middlefield

A modern kitchen is presented, featuring white cabinetry and gray countertops. Stainless steel appliances, including a microwave and gas stove, are visible. An inviting layout connects to the living area, with natural light filtering through the doorway in the background.

5 out of 5 average rating, 43 reviews

Renovated 2-bedroom Near Wesleyan-Middletown

Welcome to Middletown! We are sure you will love your stay in this newly renovated apartment. This centrally located 2- bedroom apartment sleeps 4 comfortably with a large king bed in one bedroom with a TV and full bed in another. This apartment is on the second floor. Full kitchen with laundry in unit. Walk in shower in bathroom. Off street parking available. Walking distance to shops and restaurants on Main Street, Wesleyan University (1-mile walk) and Middlesex Hospital. Easy access to Rt 9

A residential house with a welcoming front porch and manicured bushes is presented. The two-story structure features a light-colored exterior and multiple windows. A narrow driveway to the side leads to a smaller garage. The setting indicates a neighborhood atmosphere.

4.94 out of 5 average rating, 805 reviews

Quaint 2br apt- 1 block walk to Wesleyan & Main St

Nicely appointed 1st floor 2 BR apt with mid-century modern inspired decor that is a cozy home away from home. House is 1 block from Wesleyan and 2 blocks from food/fun on Main St, so you don’t need to use your car to visit Wesleyan or get to anything in town since the location is very walkable. Laundry, dishwasher, tv with roku, dvd player and dvd’s, books, bluetooth radio, wifi, front porch and back yard seating, close to Rt 9, I-91, Rt 84, Hartford and short drive to beaches/shoreline/I-95.

4.93 out of 5 average rating, 141 reviews

The spacious studio suite features a queen-sized bed, wooden flooring, and a dining area with a small table and chairs. A Smart TV is mounted on the wall opposite a well-lit kitchenette, which includes a small fridge and microwave. Soft lighting enhances the relaxed ambiance.

Guest suite in Cheshire

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10, I-691, and Route 15. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. A slightly longer drive will take you to to the beautiful shoreline, Hammonasset Beach State Park, Foxwoods and Mohegan Sun Casinos!

4.95 out of 5 average rating, 116 reviews

An open-concept living area features a cozy seating arrangement with a green leather sofa and textured accent chairs. A glass coffee table sits atop warm wooden flooring. The space is filled with natural light, with large windows showcasing views of the surrounding woods and a modern woodstove.

Home in Southington

Connecticut Chalet - Private Pond, Firepit, Views!

Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

4.97 out of 5 average rating, 98 reviews

The exterior of the cottage features a sunroom with large windows allowing ample natural light. Outdoor seating includes floral-patterned chairs surrounding a small table on a paved patio. Lush green grass surrounds the structure, enhancing the relaxed atmosphere.

Cottage in Middlefield

Anchors' Away-

Anchors Away! Is the perfect setting for a quick get away! Or a prolonged vacation! Where reading, chilling, fishing, boating are not just words--Its a state of mind!! If you were any closer to the lake, you would feel as if you were on a houseboat... Every amenity is here for you to enjoy. Convenient to Interstate 91, Merrit Parkway, RT. 9.Recently gut renovated you will find the luxury of a hotel, yet quiet enjoyment. The property has two full bedrooms-one full bath-large great room!

5 out of 5 average rating, 200 reviews

A young piglet is seen resting on a bed of straw. Its shiny black and white fur contrasts with the golden straw, while its small ears perk up. The background features blurred earthy tones, suggesting a rustic farm environment.

Guesthouse in Portland

Guesthouse Farm Stay

Come stay with us on our working farm. Relax and take in our beautiful 12-acre property while sitting on the back deck, overlooking pastures. Or for a more interactive experience, join us on a farm tour during our morning and evening farm chores. Our farm was established in 1739 with a rich history in agriculture and livestock. Our cottage is studio-style with an open bedroom, living room, and dining area. There is a kitchette and bathroom with a shower for your convenience.

5 out of 5 average rating, 126 reviews

Home in Haddam

Cozy Comforts!

Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

4.94 out of 5 average rating, 154 reviews

A clean bathroom countertop displays a crystal soap dispenser and containers holding cotton balls and swabs. A decorative tray presents a coordinating design, while fresh towels are neatly arranged nearby. The mirror reflects light, enhancing the clarity of the space.

Condo in Middletown

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

4.92 out of 5 average rating, 247 reviews

A sandy beach is viewed alongside a calm lake, with a covered picnic area featuring several wooden tables. A lifeguard chair stands prominently on the shore, while greenery and homes are visible in the background, contributing to a serene recreational setting.

Cottage in Middlefield

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

4.95 out of 5 average rating, 193 reviews

A cozy outdoor seating area features a fire table with a vibrant flame, surrounded by a stone patio and a neatly landscaped yard. A variety of plants and decorative stones enhance the natural setting, providing a serene backdrop for relaxation.

Apartment in New Britain

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

5 out of 5 average rating, 20 reviews

A modern entranceway features a large black front door with frosted glass panes, allowing natural light to brighten the space. A minimalist wall art piece adds a decorative touch, while a textured area rug lies on the polished wood floor, enhancing the welcoming ambiance.

Home in Middlefield

Charming Connecticut Hideaway

This beautifully remodeled two bedroom single family home is situated on a large private lot in the quaint town of Middlefield, Connecticut. The house is centrally located and just a short drive from Wesleyan University, Lyman Orchards, Middlesex Hospital, Lake Beseck and much more. No matter your reason for visiting the area, this home is sure to leave you feeling satisfied and wanting to return again soon.

Guest suite in Wallingford

A lush garden space is surrounded by vibrant greenery and flowering plants. A brick patio features a red umbrella over a small table and chairs, providing a shaded area for relaxation. Decorative planters enhance the tranquil setting, inviting guests to enjoy the outdoors.

5 out of 5 average rating, 591 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, private entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station.

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Other great vacation rentals in Middlefield

An outdoor seating area is organized with dark wicker furniture arranged around a central table, situated on a pea stone patio. A fire pit is visible in the background. Decorative outdoor lights and a garden torch enhance the space, surrounded by fallen leaves.

Guest suite in Cromwell

4.8 out of 5 average rating, 5 reviews

Private Guest Suite

CatieRating, 5 stars1 week ago

This stay was everything I needed. the property was clean, peaceful and well equipped. The host was very responsive to any needs and made the stay comfortable and inviting. Having access to a fire pit was a lovely touch to unwind on a clear evening.

4.94 out of 5 average rating, 414 reviews

Private room in Guilford

Tucked Away Near Lake and Hiking

RobertRating, 5 stars3 weeks ago

Beth’s place was lovely, a large pond and woods. Peaceful and quiet. Beth could not have done more to make sure we enjoyed our stay. The room is spacious and Beth made us feel right at home. And we learned a lot about the history of farming in North Guildford.

A small closet is displayed with a single wooden hanger attached to the wall. A narrow shelf unit is positioned on the right, providing space for storage. The walls are painted white, and the floor showcases wooden planks.

4.52 out of 5 average rating, 264 reviews

Private Apartment I Near Wesleyan University

JohnRating, 5 stars1 month ago

Everything as advertised. Good wi-fi. Easy access. Good kitchen and bathroom. Thanks

Home in Meriden

4.74 out of 5 average rating, 19 reviews

The hideout Studio

DerekRating, 5 stars4 days ago

I’m very cool little please exactly what we needed for the night. The only complaint I would have as he needs more towels, but beside that it was perfect for what we booked it for. The location is not what I would call vacation type spot but again was perfect for where we needed to be and met all of our needs. Steven communicated all the information we needed without having to bother him once. Would stay again.

Guesthouse in Southington

A spacious living area features a plush sectional sofa adorned with decorative pillows. A rectangular coffee table sits in the center, accompanied by a small potted plant. Natural light enters through a window, while a private entrance door is visible in the background.

5 out of 5 average rating, 6 reviews

Cozy Private Guest Suite

ElaineRating, 5 stars4 weeks ago

I had a great stay. I was looking for a place near Middletown to visit my daughter at Wesleyan University. This was about a 15 minute very easy drive. It was located in a quiet neighborhood and the pictures were a great representation of the actual place. Yassir was a very responsive host! I would stay here again.

A modern kitchen is featured with a spacious countertop and stainless steel sink. Above, elegant light fixtures provide illumination. The adjoining living area is visible, showcasing a comfortable seating arrangement and large windows allowing natural light to fill the space.

Home in Middlefield

4.81 out of 5 average rating, 36 reviews

Elegant Middlefield Getaway w/ Game Room!

CindyRating, 5 stars1 week ago

Lovely place to stay while in the area for a family reunion. Large living space open to kitchen with multiple options for seating made for an enjoyable stay for our whole group. Everyone loved it!

A wooden deck is shown, featuring a railing with metal wire accents. Sunlight casts shadows on the surface, revealing a spacious area suitable for outdoor activities. In the background, trees and a small white shed are visible, contributing to a peaceful outdoor setting.