Holiday rentals in Portland

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Top-rated holiday rentals in Portland

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Guest favourite

Flat in Middletown

5 out of 5 average rating, 52 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

Guest favourite

Flat in Middletown

4.94 out of 5 average rating, 817 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

Guest suite in Wethersfield

4.99 out of 5 average rating, 328 reviews

Bright, clean studio in charming Old Wethersfield

Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.

Top guest favourite

Home in East Hampton

5 out of 5 average rating, 25 reviews

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.

Superhost

Home in Cromwell

4.82 out of 5 average rating, 102 reviews

Cozy Mid Century home in prime location!

Enjoy an updated, mid century modern inspired, home minutes away from Wesleyan University & TPC River highlands! This eclectic space offers you a cozy retreat that is centrally located. The bedrooms have 1 King, 1 Queen, & 1 Full with luxury mattresses! High speed Wi-Fi, chefs kitchen, dedicated work desk, and garage space! A few mins from RT 9 & 91! Easy to get everywhere in CT!!! Only 5 mins to TPC, 10 mins to Wesleyan, 20 mins to Hartford! Scald protector on shower upstairs!

Top guest favourite

Guest house in Portland

5 out of 5 average rating, 223 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.

Superhost

Guest suite in Cromwell

4.92 out of 5 average rating, 12 reviews

Private Guest Suite

Private Guest Suite in a New England Cape Cod style home located in a wonderful neighborhood in Cromwell CT. Completely renovated suite. Enjoy private access to a quiet, well lit space with wonderful large illuminating windows and sky light. In-suite washer dryer, double vanity bathroom, bedroom and living room. Internet/TV provided. Bedroom- Full-size bed. Dry kitchen- a toaster oven, microwave, freezer/fridge, Keurig, and water tower. Outdoor pea stone patio, and fire pit.

Top guest favourite

Home in Haddam

5 out of 5 average rating, 129 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!

Guest favourite

Apartment in Middletown

4.93 out of 5 average rating, 161 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

Top guest favourite

Guest house in Glastonbury

4.92 out of 5 average rating, 210 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.

Guest favourite

Treehouse in Willington

4.92 out of 5 average rating, 459 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Guest favourite

Flat in Middletown

4.87 out of 5 average rating, 319 reviews

3 bedroom near Wesleyan, downtown

This updated, 1st-floor apartment in our historic home is walking distance from Main Street, restaurants, Wesleyan, walking paths, and hospital. Open kit/LR/DR for easy socializing. Access to yard. Quiet, comfortable bedrooms. We do not allow parties, only the guests listed on the reservation should be on site.