Holiday houses in Portland

5 out of 5 average rating, 45 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

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.

Superhost

Cottage in Portland

4.61 out of 5 average rating, 18 reviews

Lake Cottage Getaway

Leave your worries behind and enjoy the breath-taking view of the Great Hill Pond Lake with your own private dock! Relax on the lake and enjoy your favorite drink. This 500 sq ft cottage offers an updated kitchen, bathroom, master bedroom with full size bed, living room, sunroom & outdoor gazebo overlooking the water. Perfect for a romantic getaway, writer's retreat, or a nice getaway to just unwind and enjoy the beauty of nature. Great nearby trails & about 15 minutes to downtown Middletown.

Superhost

4.81 out of 5 average rating, 52 reviews

Cozy Apartment Near Wesleyan and Town Center

Our home is located within minutes of downtown Middletown. You can eat in our well equipped kitchen or out at any of the 5 star restaurants around town. Enjoy hopping into small boutique and major big box stores around town. Parents of Wesleyan students can enjoy visiting and come stay in a quiet apartment minutes from the campus. There are art galleries, summer theatre nearby and a nice safe place to stroll around town. If hiking is your thing, there are many marked trails around the area.

5 out of 5 average rating, 19 reviews

Home in East Hampton

CT River Retreat - Modern Home with CT River Views

Welcome to your home away from home! This charming three-bedroom, three-full-bath house is the perfect retreat for your stay in or near East Hampton, CT. Explore the charm of the area with ease, as the house is conveniently located .1 mile away from Saint Clements Castle & Marina, and 7 miles from Wesleyan University. Nestled along the picturesque Connecticut River, this inviting haven offers not only comfortable accommodations but also stunning views that will leave you breathless.

4.89 out of 5 average rating, 438 reviews

Apartment in Glastonbury

Quiet 2 bed room apt w/ private entrance.

NOTE WELL: This light, spacious basement apartment is located in a residential neighborhood in South Glastonbury near the Connecticut River and many good hiking areas, shops, and restaurants. We are working professionals who rise and retire early. We have a large exuberant dog who is fenced (electric) away from the apartment and house entrances and driveway. The space is not appropriate for parties. Do not inquire or book if your life situation is not amenable to this description.

5 out of 5 average rating, 202 reviews

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.

4.94 out of 5 average rating, 154 reviews

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

4.95 out of 5 average rating, 193 reviews

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.

Guesthouse in Glastonbury

4.92 out of 5 average rating, 204 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

4.93 out of 5 average rating, 113 reviews

Private Downtown Oasis

Private First Floor Rear Apartment of an 1849 historical home in the heart of Middletown, CT. One block walk to Wesleyan University with private parking. Main street also one block away with many great restaurants, and our best local coffee shop (Klekolo) just doors away from your apartment. The House is across from the public library. Stone patio in a lovely fenced in rear yard.

Guest suite in Glastonbury

4.98 out of 5 average rating, 46 reviews

Huge studio with washer and dryer separate entry

Ground level in-law studio apartment. Suite includes queen bed, living area, kitchenette, bedroom & FULL bathroom. Washer & dryer. Your own thermostat too! The kitchenette includes refrigerator, dishwasher, microwave, air fryer and Keurig. There is no cooktop/stove or oven. PLEASE SEND INQUIRY IF YOUR DESIRED DATES ARE NOT AVAILABLE!

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Other great holiday rentals in Portland

Superhost

Private room in Portland

4.69 out of 5 average rating, 68 reviews

Acorn Acres - 1 King Master Suite Daily Rates

LouiseRating, 5 stars3 weeks ago

The suite at Lucas' place was just as described, with a gorgeous view of yard and woodlands. Very quiet and peaceful. We appreciated Lucas' flexibility (we arrived later than anticipated) and good communication. We were at Wesleyan for a graduation, so if anyone is looking for a place to stay that's close to Middletown (about 15 min away), I'd recommend Lucas' place.

5 out of 5 average rating, 16 reviews

Apartment in Manchester

Humble Abode

RachelRating, 5 stars6 days ago

Such a cute place! Walking distance to a paved walking trail, which I really enjoyed in the morning! Safe neighborhood, well lit entrance and cozy place. Brand new build and very clean. Would stay again!

4.97 out of 5 average rating, 70 reviews

Apartment in Manchester

Cozy 1 bedroom clean and quiet

CharlesRating, 5 stars5 days ago

Enjoyed my stay here. I Recommend it to folks visiting the Hartford area.

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

Private room in Colchester

4.99 out of 5 average rating, 233 reviews

Secluded colonial in an idyllic country setting

CatherineRating, 5 stars1 week ago

Marianna Was warmly welcoming, serving us cheese and snacks. She carried my heavy bag up to our rooms which were beautifully decorated, so very, very clean ! It was a hot humid day and we just relaxed in the central air conditioning. We will definitely be returning. Catherine

Private room in West Hartford

4.97 out of 5 average rating, 175 reviews

Quiet, clean home, private room and bath

KateRating, 5 stars1 day ago

I had a great stay while in the Hartford area for work. Denise was lovely and welcoming. I will be back!

4.88 out of 5 average rating, 266 reviews

Private room in Hartford

Charming & Cozy

AlexisRating, 5 stars3 weeks ago

I only have good things to say about Stephanie's place! Although I was out and about most of the time, the space itself was very quiet and peaceful to come back to at night. There were many written notes and reminders around the house, which is very helpful when you are staying in an unfamiliar place. Check-in/check-out was straight-forward and efficient. You will feel very comfortable here!