Vacation rentals in Portland

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Top-rated vacation rentals in Portland

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

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Guest favorite

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.

Guesthouse in Portland

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.

ValueFamilyGrill

4.97 out of 5 average rating, 358 reviews

Top guest favorite

The living room features a large Smart TV above a fireplace, complemented by a cozy area rug. Various seating options include a white leather sofa and two reclining chairs. Sunlight filters through sheer curtains, enhancing the inviting ambiance of the space.

Home in Middletown

Family Stays, CT

Centrally located - just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and generous space for groups. With 4 bedrooms across two floors, the layout lets everyone spread out. Bedrooms on separate levels provide natural privacy while still enjoying one shared home. Whether you're traveling with friends, children, extended family, or multiple couples, the 2‑floor setup helps everyone relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

ValueLocationHospitality

4.99 out of 5 average rating, 145 reviews

Top guest favorite

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.

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.

LocationValueOutdoor spaces

4.94 out of 5 average rating, 923 reviews

Guest favorite

A modern kitchen features sleek white cabinetry and a stone countertop. Stainless steel appliances, including a refrigerator and washer/dryer combo, are present. A large window allows natural light, while a textured area rug adds warmth to the space. Ample storage is available throughout.

Apartment in Middletown

Updated 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

ValueFamilyKitchen

4.96 out of 5 average rating, 108 reviews

Guest favorite

A serene lakeside house is framed by lush greenery, with a wooden dock leading to the water. The porch, adorned with large windows, provides an inviting entrance. The structure features a classic design, complemented by natural surroundings, ideal for enjoying scenic views and outdoor activities.

Home in East Hampton

Beautiful lakefront home, 4bed 2.5ba

80ft of lakefront. Perfect for summer water activities, stunning fall foliage and ice skating in the winter! East-facing with stunning sunrises. Very well equipped kitchen, cosy sitting room & wood-burning stove, dining room and 1/2 bath. Large porch faces lake, with sitting area and dining table. Ground floor king-size master & bathroom, with stunning lake views. Upstairs 3 queen bedrooms, all w lake views and ample closet space. TVs in 3 bedrooms + projector/screen for movie watching.

FamilyLocationWalkability

4.86 out of 5 average rating, 150 reviews

Top guest favorite

A tranquil lake scene is captured at sunrise, featuring a wooden dock extending into the water. Soft pink and orange hues reflect on the lake's surface, complementing the surrounding greenery. Two Adirondack chairs sit near a fire pit, inviting relaxation by the scenic view.

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.

ValueFamilyComfort

4.93 out of 5 average rating, 363 reviews

Guest favorite

The image captures a serene lake view, highlighting the calm water reflecting the blue sky and distant hills. A wooden dock is visible in the foreground, with a gentle shoreline leading to lush greenery. The landscape is peaceful, surrounded by trees and residential buildings in the distance.

Cottage in Portland

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.

LocationValueAccess

4.8 out of 5 average rating, 35 reviews

Guest favorite

A welcoming living room features a comfortable couch and two textured armchairs, arranged around a central round coffee table. Natural light filters through large windows, highlighting a cozy atmosphere. A small side table displays a plant and a soft throw blanket.

Home in New Britain

Bright & Private WHOLE HOUSE 4 YOU Near Everything

Welcome to our clean, bright, and private home, just a 15-minute drive from the heart of Hartford! Designed with your comfort and convenience in mind, this cozy retreat is perfect for families, couples, and professionals looking for a peaceful yet central stay! Prime Location, WHOLE HOUSE – Explore New Britain & Beyond! Guest Access: ✔ Private driveway for easy parking ✔ Enclosed garage with keyless entry for secure parking ✔ Keyless pad entry at the front door (host will provide the code)

LocationFamilyCheck-in

4.95 out of 5 average rating, 122 reviews

Top guest favorite

A welcoming entrance features a wooden door with decorative glass, flanked by a star accent and an octagonal window. Two chairs with vibrant striped cushions are placed on a patterned rug, accompanied by potted plants and colorful flower baskets, creating an inviting atmosphere.

Guest suite in Middletown

Guest Suite, 2nd floor, 3 bedrooms, near Downtown!

Close to Downtown Middletown & Wesleyan University, located between Hartford & New Haven. Private floor with 3 bedrooms - two bedrooms have queen beds, third bedroom also serves as a living room with a sleeper sofa, listing sleeps 6 total. Large bathroom with double sinks & shower (no tub). NO KITCHEN but there is a mini-fridge, microwave & Keurig, with coffee, tea, water & supplies provided. Perfect for Wesleyan parents, students & visitors, couples, families, wedding & business travelers.

LocationFamilyLong stay

4.98 out of 5 average rating, 164 reviews

Top guest favorite

The house features a modern black exterior with large windows that welcome natural light. A set of wooden steps lead to the main entrance, flanked by a deck that extends toward the surrounding landscape. A detached garage is visible in the background.

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.

LocationFamilyLayout

5.0 out of 5 average rating, 72 reviews

Top guest favorite

The farmhouse is depicted with a well-maintained exterior, featuring a symmetrical design and light-colored siding. Vibrant purple and pink flowers bloom in front, adding color to the landscape. A rustic barn is visible in the background, surrounded by lush greenery and a clear blue sky.

Farm stay in Glastonbury

Classic Farm House on a Working Farm & Vineyard

This quaint farmhouse will be your home away from home. Enjoy the scenery and explore local attractions. The farm house is situated just feet from Joseph Preli Farm and Winery (also owners of the farmhouse) with its bountiful grapevines, fruits and vegetables. The farm and vineyard is known for it's old-world Italian charm. Family owned for 100 years, they respect history by using traditional farming methods and antique tractors. See updates about the farm and winery at @jprelifarm

FamilyLocationDecor

4.97 out of 5 average rating, 118 reviews

Top guest favorite

The open living area features a cozy seating arrangement with two light blue chairs and a stylish coffee table. A propane fireplace serves as a central focal point, surrounded by warm lighting and natural decor. A small work area with a desk is positioned near a window, offering views of the outdoors.

Cottage in East Hampton

Family Friendly Lake House Lake Pocotopaug Sunsets

Enjoy this newly renovated and beautifully decorated lakefront retreat! With stunning sunsets and breathtaking views, this charming 3-bedroom, 2-bathroom cottage offers a peaceful escape. Cozy indoor and outdoor spaces—including a unique undersea mermaid mural—invite relaxation. With all the comforts of a larger home, plus direct water access for kayaking and paddleboarding, it’s the perfect place to unwind and make lifelong memories.

FamilyValueSleep quality

5.0 out of 5 average rating, 70 reviews