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Holiday rentals in Portland

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Top-rated holiday rentals in Portland

Guests agree: these stays are highly rated for location, cleanliness and more.

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Rental unit in East Haddam

4.78 out of 5 average rating, 268 reviews

The Federal Suite at the Wisteria Rest

The apartment is beautiful and fully furnished in the historic District of East Haddam close to Rt 9 or 2, the Goodspeed Opera House, River House and CT Shoreline. Gillettes Castle, Fox Hopyard, Devils Hopyard, & more. Just 20 minutes to Middletown and wonderful dining. This apartment is in the 1800 section and has some quirky things to be aware of, floor that have uneven heights, stairs to the bedroom and , a claw foot tub/shower that you have to step into and a full flight of stairs to get in.

Guest favourite

Rental unit in Middletown

4.94 out of 5 average rating, 744 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.

Guest favourite

Guest suite in Wethersfield

4.99 out of 5 average rating, 280 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.

Guest favourite

Guest house in Glastonbury

4.94 out of 5 average rating, 139 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Guest favourite

Apartment in Middletown

4.96 out of 5 average rating, 126 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 kichen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking, swimming pool. 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 favourite

Rental unit in Glastonbury

4.9 out of 5 average rating, 418 reviews

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.

Guest favourite

Guest house in Portland

4.99 out of 5 average rating, 135 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.

Cabin in East Haddam

4.9 out of 5 average rating, 572 reviews

Getaway Machimoodus - NYC/Boston

An easy drive from the city, Getaway is a new way to experience the great outdoors. Nestled across dozens of acres of private woodlands, our modern, tiny cabins have everything you need (comfy bed, bathroom, fresh linens) and nothing you don’t. Featuring a private outdoor area (hello, fire pit), each cabin is designed to help you relax, unwind and disconnect from the everyday. Plus, as part of your stay, you'll receive firewood, a s'mores kit, coffee and bottled water*.

Guest favourite

Rental unit in East Haddam

4.9 out of 5 average rating, 137 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Guest favourite

Guest suite in Wallingford

5 out of 5 average rating, 526 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 favourite

Guest house in Glastonbury

4.92 out of 5 average rating, 190 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

Rental unit in Middletown

4.82 out of 5 average rating, 147 reviews

Lakeside apartment 2.5 miles from Wesleyan campus!

Walk out to your private deck from either the living room or the kitchen. Newly-refurbished apartment in a beautiful, peaceful setting on small lake, suitable for swimming or fishing. Enjoy free use of our paddleboat! This is an in-law apartment attached to our home, so we will be nearby to help with any issues that may arise during your stay.

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Popular amenities for Portland holiday rentals

Free parking on premises

Air conditioning

Stay near Portland's top sights

Brownstone Exploration & Discovery Park25 locals recommend

Arrigoni Winery19 locals recommend

Dinosaur State Park17 locals recommend

O'Rourke's Diner12 locals recommend

Crystal Ridge Winery10 locals recommend

Kidcity Children's Museum9 locals recommend

Other great holiday rentals in Portland

Guest favourite

Home in Andover

5 out of 5 average rating, 45 reviews

Spacious modern lakefront home with jet tub

Guest favourite

Farm stay in Glastonbury

4.87 out of 5 average rating, 15 reviews

The Farmhouse at Roses Farm

Guest favourite

Rental unit in Manchester

4.87 out of 5 average rating, 31 reviews

Manchester Oasis Downtown Main St. Pet-Friendly!

Guest favourite

Guest house in East Hampton

4.87 out of 5 average rating, 52 reviews

Your Own Barn Loft Suite Among the Treetops

Guest favourite

Home in East Hampton

5 out of 5 average rating, 20 reviews

The Little Nest Cottage at Lake Pocotopaug

Home in Meriden

4.79 out of 5 average rating, 38 reviews

Private Deluxe Studio

Guest favourite

Home in Middletown

4.93 out of 5 average rating, 56 reviews

Home away from home

Guest suite in Rocky Hill

4.69 out of 5 average rating, 51 reviews

Fully Furnished In-Law Suite in Rocky Hill

Quick stats about holiday rentals in Portland

Total rentals
20 properties
Nightly prices starting at
£38 before taxes and fees
Total number of reviews
1.3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi

Destinations to explore