Places to stay in Portland

4.94 out of 5 average rating, 805 reviews

Apartment in Middletown

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.

4.95 out of 5 average rating, 222 reviews

Home in East Haddam

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

4.87 out of 5 average rating, 101 reviews

Beautiful Lake House on Lake Pocotopaug

Enjoy a relaxing vacation in a beautiful, updated lakefront home on Lake Pocotopaug. Summer =grilling out, kayaking & paddle boarding with family & friends. A lakeside marina offers party boat rides & kayak rentals. Winter=relaxation by the cozy fireplace, games and ice skating when the lake freezes over. Projector Screen, Games, Books, AC, Heat, Outdoor Grill and a working fireplace. All year round, we'd love to have you at our home. which we love and use as a getaway from the city.

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, 200 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.

5 out of 5 average rating, 126 reviews

Home in Haddam

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!

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.

Guest suite in Wallingford

5 out of 5 average rating, 591 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.

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

Apartment in Middletown

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.

4.82 out of 5 average rating, 163 reviews

Apartment in Middletown

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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Other great vacation rentals in Portland

4.96 out of 5 average rating, 26 reviews

Home in Rocky Hill

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

TanyiaRating, 5 stars5 days ago

I would like to stay Lisa’s property looked just like the pictures, but it was honestly even better! We have been to many nice Airbnbs but this was the nicest. It was the special touches that were so thoughtful….beautiful fresh roses in the kitchen and bathroom, battery candles that came on in the evening, muffins, snacks, dog treats, shower steamers. So very welcoming. We had such a relaxing few days. The home is extremely clean with very comfortable decor and bedding and lovely thick bath towels. The master bath is spa like. We enjoyed sitting out on the huge deck while my son was fishing right across the street. If we get back to the area, we would stay here again in a heartbeat. Thanks so much Lisa for having us.

4.84 out of 5 average rating, 128 reviews

Beautiful lake-front, 4 bedrooms, 2.5 bathrooms

LisaRating, 5 stars6 months ago

Our stay at Vanessa's house was tranquil and picturesque. The washing machine broke down a few days before our arrival, but Vanessa remained on top of it, and made sure it was in working order before we checked in, which we appreciated tremendously. We couldn't beat the view of the water and only wish it had been a bit warmer so that we could have appreciated the gorgeous back porch area. Thank you, Vanessa!

4.98 out of 5 average rating, 103 reviews

Classic Lake House~4 Steps to water_FirePit_kayaks

AmandaRating, 5 stars2 months ago

We had a fantastic time at Marian’s place. Our guests were my husband, 1 yr old and I, my parents and sister. The moment we walked into the home my Dad said “I feel so relaxed!” I wanted to give a shoutout to the cleanliness of the place. It was absolutely spotless, and we have really high standards— my parents were custodians in a different life! Finally, the space is very family friendly. Closets had a baby bath and high chair. These touches make it so much easier traveling with a child! Thank you Marian! We will be back!

4.99 out of 5 average rating, 72 reviews

Lake Fun: PingPong, Pool Table, Slide, EV Charger

KylieRating, 5 stars1 week ago

We had a wonderful stay at this gorgeous lakehouse! Honestly, the pictures don't do the place justice. The lake was lovely, and the house was well-equipped and spotlessly clean. The furnishings and decorations were far nicer than you often find in an airbnb; it felt like a true home. Everything we could have possibly needed to enjoy the lake was provided, from canoes and kayaks to inner tubes, and the kitchen was well-equipped with all manner of cooking utensils and basic spices/condiments. Linda and Dick were great--very communicative and easy to get ahold of, but left us to our privacy otherwise. Would absolutely go back again!

4.97 out of 5 average rating, 29 reviews

Home in Haddam

The Farmhouse Stay

MarisaRating, 5 stars3 weeks ago

Chelsea was communicative and helpful about her beautiful house. It had all we needed, was well appointed, beautifully decorated and in a gorgeous natural setting. We spent time lounging in the living room as a family and it was so comfortable. Top notch! Grab this place now!

5 out of 5 average rating, 41 reviews

Home in New Britain

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

CesarRating, 5 stars1 day ago

me and kids was there for a mini getaway and everyone had their on bed which was dope a.f..my 10 yo nephew played on trampoline..for extended stay she has washer and dryer (we spent one night didn't use it) only complaint I have is when I took a shower it was a leaning curve with the water temp I couldn't figure the thing out my kid had to help me figure it out besides that place is great imo

4.9 out of 5 average rating, 41 reviews

Waterfront Lake House

DaviaRating, 5 stars1 month ago

Lovely home and lovely host. Stayed here for my sister’s graduation at UCONN and it was very beautiful. Loved the lake view!