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.

Guest favourite

Guest suite in New Britain

4.92 out of 5 average rating, 130 reviews

Clean, Quiet and Safe w/Amenities to spare!

This newly renovated in-law apartment (basement) has a private entrance and Ring security protection in the quaint, quiet neighborhood bordering Berlin/New Britain. Come relax, enjoy biking trails, local restaurants and public parks. Renovated with attention to detail, this place has all the comforts of home. Includes two flat screen TVs in bedroom and living room with Fire sticks (cable/movies), two fireplaces and granite vanity & breakfast bar. Working professionals get 10% off long term stays

2–9 Jul

£95 per night
Guest favourite

Flat in Middletown

4.94 out of 5 average rating, 695 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.

6–13 Dec

£112 per night
Guest favourite

Guest suite in Wethersfield

4.99 out of 5 average rating, 247 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.

24–31 Jul

£109 per night

Popular amenities for Portland holiday rentals

Stay near Portland's top sights

Mondo4 locals recommend
Brownstone Exploration & Discovery Park25 locals recommend
Inn at Middletown3 locals recommend
Metro Movies 127 locals recommend
Arrigoni Winery19 locals recommend
Eggs Up Restaurant4 locals recommend

Other great holiday rentals in Portland

Guest favourite

Cottage in Middlefield

4.93 out of 5 average rating, 228 reviews

Lake Beseck cottage

1–8 Feb

£163 per night
Guest favourite

Guest house in Portland

5.0 out of 5 average rating, 58 reviews

Guesthouse Farm Stay

26 Aug – 2 Sept

£138 per night
Guest favourite

Farm stay in Glastonbury

5.0 out of 5 average rating, 50 reviews

Historic Farmhouse by the River (Duplex)

5–12 Nov

£114 per night
Guest favourite

Apartment in Middletown

4.97 out of 5 average rating, 99 reviews

Entire place to yourself Cromwell/Middletown Line

24–31 Oct

£116 per night
Guest favourite

Home in Haddam

5.0 out of 5 average rating, 69 reviews

Cozy Comforts!

28 Jun – 5 Jul

£154 per night
Guest favourite

Guest suite in Portland

4.91 out of 5 average rating, 11 reviews

Cozy waterview in-law apartment

10–17 Jun

£132 per night
Guest favourite

Home in East Hampton

4.98 out of 5 average rating, 49 reviews

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

15–22 Dec

£314 per night
Guest favourite

Home in East Hampton

4.94 out of 5 average rating, 17 reviews

Waterfront Lake House

26 May – 2 Jun

£584 per night
Guest favourite

Holiday home in East Hampton

5.0 out of 5 average rating, 21 reviews

Family Friendly Lakefront Sunsets

17–24 Sept

£432 per night
Guest favourite

Flat in New Britain

4.96 out of 5 average rating, 80 reviews

Spacious Cozy Guest Suite

14–21 Oct

£87 per night
Guest favourite

Home in East Hampton

5.0 out of 5 average rating, 56 reviews

🌅A Sunrise Lake Retreat for Couples or Families🌅

3–10 Dec

£541 per night
Guest favourite

Home in Glastonbury

5.0 out of 5 average rating, 34 reviews

Glastonbury home, Large Porch, Peloton & Pets OK

11–18 Feb

£233 per night

Quick stats about holiday rentals in Portland

Total rentals

20 properties

Popular amenities

Kitchen, Wifi and Pool

Wifi availability

10 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

1.2K reviews

Nightly prices starting at

£40 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Middlesex County
  5. Portland