Vacation rentals in Middlefield

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Top-rated vacation rentals in Middlefield

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Top guest favorite

A spacious deck is shown, featuring a grill and outdoor seating. Large glass doors lead into the studio, while the wooden flooring adds a rustic charm. The surrounding natural greenery provides a peaceful view, enhancing the outdoor experience.

Guest suite in Durham

4.9 out of 5 average rating, 40 reviews

Spacious Studio in quiet neighborhood.

Quiet, rural setting. Surrounded by nature in a historic town. Spacious (500 square feet) private studio. Queen bed ( pack ‘n play & high chair on request) Full kitchen & full bath. Large deck, off street parking. Conveniently located half way between NYC and Boston. You can be in either in about 2 hours. An hour from RI beaches . A very central location. Connecticut has much to see and explore. The Connecticut River, the Housatonic River and our extensive shoreline. So much to see and do!

Guest favorite

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.

Apartment in Middletown

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.

Top guest favorite

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

4.93 out of 5 average rating, 143 reviews

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!

Guest favorite

A dining area features a wooden table surrounded by dark chairs, set with blue and white plates. Large windows allow natural light and provide an expansive view of the lake, where boats can be seen in the distance.

Cottage in Middlefield

4.97 out of 5 average rating, 98 reviews

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!

Top guest favorite

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

5 out of 5 average rating, 203 reviews

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.

Guest favorite

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

4.94 out of 5 average rating, 155 reviews

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

Guest favorite

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

4.92 out of 5 average rating, 247 reviews

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.

Top guest favorite

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

4.95 out of 5 average rating, 194 reviews

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.

Guest favorite

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

5 out of 5 average rating, 20 reviews

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.

Top guest favorite

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.

Guest suite in Wallingford

5 out of 5 average rating, 592 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.

Guest favorite

An open living space features a cozy sleeping area with a spacious bed, accompanied by a modern kitchenette and seating area. Exposed wooden beams and a rustic ceiling create a warm ambiance, while a plush gray sofa adds comfort. Natural light flows in through strategically placed windows.

Loft in Durham

4.9 out of 5 average rating, 79 reviews

The Durham - Circa 1900s Dairy Farm

PRIVATE Luxury studio apartment -attached to 1900s farmhouse set on 4 acres. Modern farmhouse style! Enjoy the peaceful town of Durham, CT. [private entrance, patio area and unit] Wonderful weekend getaway or a great alternative to hotel living while traveling for business. Private deck with gas fire and grill. 4 minutes to I91 close to Wallingford, Middletown, Hartford and New Haven.

Top guest favorite

A welcoming porch area is showcased, featuring four white rocking chairs arranged on a covered deck. The dark exterior of the house is complemented by neutral shutters on the windows. A manicured lawn extends in front of the porch, providing a relaxing outdoor space.

Apartment in Wallingford

4.97 out of 5 average rating, 379 reviews

Spacious in-law apartment steps from Choate

Private apartment with private entrance. This cute apartment is located in the center of town, close to Choate Rosemary Hall and downtown Wallingford. Very safe and charming neighborhood. Off street parking included. The private space includes a combination living, dining room, and full kitchen. Private bathroom with clean shower and amenities. Beautiful backyard with a pretty patio

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Popular amenities for Middlefield vacation rentals

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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

4.88 out of 5 average rating, 8 reviews

Private Guest Suite

CollRating, 5 starstoday

Marc-Anthony was a very responsive and helpful host. The attached apartment where we stayed was clean and very nicely finished. The water, coffee and tea provided were a nice touch. Our only mishap was the bed size, which was totally my fault. It is listed as a full size in the description which I missed. Other than a tight sleep, it was perfect. It was a restful retreat for us after the Travelers Golf Tournament!

Home in Meriden

4.67 out of 5 average rating, 21 reviews

The hideout Studio

DerekRating, 5 stars1 week 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.

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.

Apartment in Middletown

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

Guest favorite

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.

Guesthouse in Southington

5 out of 5 average rating, 6 reviews

Cozy Private Guest Suite

ElaineRating, 5 stars1 month 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, 37 reviews

Elegant Middlefield Getaway w/ Game Room!

CindyRating, 5 stars2 weeks 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!

Top guest favorite

A keypad entry system is shown installed on a green door. The lock features a digital keypad with numbered buttons and a traditional keyhole below. A brass doorknob is visible, providing convenient access.

Private room in East Haven

4.87 out of 5 average rating, 232 reviews

Cozy private room on lovely, quiet street

BettyRating, 5 stars2 weeks ago

Jeff’s place is the best place to stay when I visit New Haven. It makes me feel like I'm right at home!

Top guest favorite

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.

Apartment in Middletown

4.97 out of 5 average rating, 38 reviews

Your Sweet Spot in Middletown CT

BradenRating, 5 stars5 days ago

Originally from the area and back for the first time in 8 years for a wedding, we needed a place that was centrally located to all the friends, family, and events we had to cram into a 5-day stay. "Your Sweet Spot" perfectly fit the bill! We didn't need anything large or luxurious, basically just a place to sleep and have a cup of coffee in the morning and hit the road. The place is convenient to all the major roads and highways in the area, yet in an extremely quiet and peaceful neighborhood. It was spotlessly clean--honestly, cleaner than any rental we have ever stayed in. The bed was neither too soft nor too hard; it was just right, and we slept better than we do at home! Everything a single traveler or couple could need was available, and the deck was a perfect place to enjoy that cup of coffee and watch the birds and squirrels in the morning. Met one of the hostesses and she was a lovely person. We loved our stay, and hope it is available again next time we come to town!

Top guest favorite

A spacious room is featured, showcasing an angled ceiling with light-colored walls. A colorful dresser is positioned against one wall, while a desk with an office chair stands nearby. Natural light streams in through a window above a radiator, enhancing the quiet ambiance.

Private room in Hamden

4.97 out of 5 average rating, 472 reviews

Spacious room with private bathroom

ShahanRating, 5 stars1 week ago

Lauren is a great host . My stay was great . Her recommendation on the local information was really helpful. Enjoyed every bit of my staying . Hope to book it again for my next visit .

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Vacation rentals in Middlefield

Top-rated vacation rentals in Middlefield

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Popular amenities for Middlefield vacation rentals

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