Holiday rentals in Durham

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Top-rated holiday rentals in Durham

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Guest favourite
A charming cottage features wood shingle siding and a neatly arranged entrance. The front yard showcases a manicured area with green grass, accompanied by a duck and a chicken. Nearby, expansive fields and a rustic barn complete the serene rural landscape.
Guest house in Portland
4.98 out of 5 average rating, 257 reviews

Guesthouse Farm Stay

Come stay with us on our historic working farm! Relax on the back deck and enjoy views of our 12-acre property and peaceful pastures. For a more hands-on experience, join us for a tour to get a closer look at life on the farm. Established in 1739, our farm has a rich history in agriculture and livestock. The cozy studio-style cottage features an open living space with combined bedroom, living, and dining area, along with a kitchenette and bathroom with a shower for your comfort and convenience.

Guest favourite
A serene bedroom includes a spacious bed dressed in neutral linens, accented with a textured throw and decorative pillows. Natural light filters in through a window, and a soft area rug complements the decor. A modern chair and bedside tables enhance the inviting space.
Flat in Meriden
4.91 out of 5 average rating, 35 reviews

Hillside Retreat

Welcome to our little hillside hollow, tucked away on the east side of Meriden. I am a gardener and enjoy cultivating a wildlife habitat on our property. The retreat has been carefully designed for tranquility. It features a galley kitchen with a reading nook, a tiled bathroom, and a sweet bedroom with a small private deck overlooking the back yard, trees, and walking path. While the retreat feels rural, it is convenient to downtown, and to the noted hiking trails in the center of the state.

Top guest favourite
A bright living space is showcased with wooden floors and white walls. A dark leather sofa faces a wooden coffee table, while a rocking chair invites relaxation. A dining area features a table with four orange chairs, complemented by natural light from nearby windows.
Flat in Middletown
4.94 out of 5 average rating, 845 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 favourite
A studio layout features a queen-sized bed with neutral bedding, situated under a sloped ceiling with recessed lighting. A small dining table and two chairs are positioned near a closet. A Smart TV is mounted on the wall, complementing the wooden flooring.
Guest suite in Cheshire
4.94 out of 5 average rating, 175 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 favourite
A modern kitchen is presented, featuring white cabinetry and granite countertops. Essential appliances, including a stainless steel refrigerator and dishwasher, are visible. A small rug lies on the light wood floor, while a doorway to the dining area can be seen to the right.
Flat in Middletown
5 out of 5 average rating, 7 reviews

Cozy 1-Bedroom Wesleyan-Middletown

Welcome to Middletown! We are sure you will love your stay in this newly renovated unit. This centrally located 1- bedroom apartment sleeps 2 comfortably with a large Queen bed with a TV and a futon in the living room for 1 more guest. This apartment is on the first floor. Full kitchen with laundry in unit. Bathroom has a tub. Off street parking available. Walking distance to shops and restaurants on Main Street, Wesleyan University (1-mile walk) and Middlesex Hospital. Easy access to Rt9t

Top guest favourite
Two comfortable leather recliners are positioned in the foreground, complemented by decorative blue and floral pillows. A soft area rug lies beneath them, and the background reveals a well-equipped kitchen with wooden cabinetry and stainless steel appliances.
Guest suite in Durham
4.92 out of 5 average rating, 48 reviews

Spacious Studio in quiet neighborhood.

Quiet, rural setting. Surrounded by nature in a historic town. Spacious (500 square feet) private studio. Queen bed, fold away cot plus ( pack ‘n play & high chair upon 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, and an hour from RI beaches. A very central location, Connecticut has much to see and explore. Visit the CT & Housatonic River, plus our extensive shoreline.

Top guest favourite
The exterior of a bright red carriage house is surrounded by lush gardens filled with various flowers and greenery. Two large windows and a white door are visible, adding charm to the traditional New England design. A well-maintained lawn complements the vibrant landscape.
Guest house in Wallingford
5 out of 5 average rating, 135 reviews

The Garden Loft - A Charming Choate Stay

Welcome to The Garden Loft! Located in the heart of downtown Wallingford, CT. This traditional and historic New England carriage house has been completely renovated in the summer of 2022 into a peaceful, cozy, bright & airy loft. We are a 3 minute walk from downtown where you will find a variety of restaurants, bars, a brewery & only 1 mile from from Choate Rosemary Hall. A 15 minute drive to Yale University & downtown New Haven. Get ready to relax, get cozy & enjoy The Garden Loft!

Top guest favourite
An open-concept living space features light-colored wood flooring and a cozy seating area with a white couch and wooden coffee table. A small dining table is positioned nearby, while a stylish staircase leads to an upper level. A television is mounted on the wall, adding to the modern atmosphere.
Home in Haddam
5 out of 5 average rating, 138 reviews

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!

Top guest favourite
A comfortable living area features a gray sofa positioned around a low coffee table. A television rests on a media console against the wall, with natural light streaming through two windows that overlook greenery outside.
Home in Higganum
5 out of 5 average rating, 36 reviews

The Doll House

Enjoy the Connecticut River Valley at this cozy retreat close to where you want to be. Conveniently located near Route 9, the Doll House is easy to get to from Middletown, the shoreline, and Central CT. Enjoy the patio while having dinner or just taking in the outdoors. Take advantage of all the area has to offer, from hiking, to shows at the Goodspeed Opera House, and fine dining options in Downtown Middletown. Enjoy this private setting surrounded by nature.

Superhost
A modern kitchen is presented with sleek cabinetry and a large island. Stainless steel appliances, including a refrigerator and a microwave, are featured. Natural light streams through a nearby window, while a decorative table setting includes four place settings and a bowl of green apples.
Home in Middlefield
4.81 out of 5 average rating, 32 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 favourite
An elegant Arts & Crafts bungalow showcases a blend of architectural styles under a clear blue sky. The inviting façade features a distinctive porch, a brick chimney, and a nearby garage. Lush gardens adorned with vibrant plants enhance the home’s outdoor appeal.
Guest suite in Wallingford
5 out of 5 average rating, 621 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.

Top guest favourite
The welcoming exterior of a classic two-story home is showcased, featuring dark siding and white shutters. A well-maintained pathway leads to the entrance, illuminated by a lamp post. Rocking chairs are visible on the porch, with light spilling from the windows, suggesting a cozy atmosphere.
Flat in Wallingford
4.96 out of 5 average rating, 398 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

Popular amenities for Durham holiday rentals

  1. Airbnb
  2. United States
  3. Connecticut
  4. Durham