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The best vacation rentals in Portland

Check out our selection of great vacation rentals in Portland

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Olympic Village Vela - Portland is located in Portland, just a 3-minute walk from Portland Beach and 20 miles from Monkey World.

Review score
Wonderful
44 reviews
Price from
€ 304.97
1 night, 2 adults

The George B & B offers accommodations in Weymouth, a 7-minute walk from Weymouth Beach and 15 miles from Monkey World.

Great breakfast, clean rooms, very generous tea, coffee, biscuits, plenty of soap and shampoo, friendly staff.
Review score
Wonderful
1,072 reviews
Price from
€ 136.46
1 night, 2 adults

Housed in a historic building, the recently renovated Kelston Guest House offers accommodations with a shared lounge and free Wifi.

Clean, comfortable well-appointed room. Lovely hosts. Great breakfast.
Review score
Wonderful
347 reviews
Price from
€ 93.75
1 night, 2 adults

On Weymouth Esplanade, The Edenhurst is on Dorset’s Jurassic Coast. It is within easy reach of the Sea Life Center, Northe Fort, and the Harbor.

Great service with warm greeting, great assistance for getting baggage to room Pre booked full English breakfast in sunny breakfast room was very pleasant, View from the bedroom window was outstanding looking out across the bay
Review score
Wonderful
597 reviews
Price from
€ 142.40
1 night, 2 adults

Hudsons Guest House - Adults only enjoys a location in Weymouth, a 19-minute walk from Weymouth Beach and 15 miles from Monkey World.

Fantastic, nice host friendly charming made me feel very welcome and relaxed.
Review score
Wonderful
436 reviews
Price from
€ 96.12
1 night, 2 adults

Birch House Bed & Breakfast offers accommodations in Weymouth, 1.6 miles from Weymouth Beach and 16 miles from Monkey World.

The breakfast was very good , more than enough for us. The place was clean and comfortable and the landlady very friendly.
Review score
Wonderful
232 reviews
Price from
€ 130.53
1 night, 2 adults

Marjune Guest House enjoys a location in Weymouth, 1.2 miles from Weymouth Beach and 15 miles from Monkey World. This 3-star guest house offers daily room service and private check-in and check-out.

The bed was really comfortable. The room was cozy and well stocked with teas and coffees, toiletries and large bath towels. The breakfast was delicious with a large selection of cooked options, cereals, toast, croissants, etc. The hostess, Stephanie, was very welcoming and friendly. A really enjoyable stay.
Review score
Exceptional
429 reviews
Price from
€ 120.09
1 night, 2 adults

A 13-minute walk from Weymouth Harbor, Gloucester House is located in Weymouth and features a shared lounge and free WiFi.

Great breakfast, location near train, very comfortable and spacious. Extremely clean
Review score
Exceptional
369 reviews
Price from
€ 176.81
1 night, 2 adults

Braemar offers accommodations in Weymouth, 15 miles from Monkey World and 23 miles from Corfe Castle.

Amazing location. Our room had a view right over the beach with lovely sash windows to have the sea breeze in the morning. Really friendly hosts showed us around the property and were happy to help if needed.
Review score
Wonderful
487 reviews
Price from
€ 83.07
1 night, 2 adults

Cornubia Guest House enjoys a location in Weymouth, 1.2 miles from Weymouth Beach and 15 miles from Monkey World.

Great Hosts
Review score
Wonderful
410 reviews
Price from
€ 106.80
1 night, 2 adults
All vacation rentals in Portland

Most booked vacation rentals in Portland this month

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Enjoy breakfast in Portland!

  • Breakfast options
    Review score
    Wonderful · 8 reviews

    Lyme View offers accommodations in Portland, a 11-minute walk from Portland Castle and 2.1 miles from Portland Museum.

  • Review score
    Wonderful · 7 reviews

    Vindelis Cottage Chesil Beach is located in Portland, just 24 miles from Golden Cap and 28 miles from Corfe Castle.

  • Review score
    Wonderful · 13 reviews

    Bright & beautiful 4 bedroom house with sea views offers accommodations in Portland, a 3-minute walk from Portland Beach and 5 miles from Weymouth Harbour.

  • Review score
    Wonderful · 10 reviews

    Seascape Apartment offers accommodations in Portland, a 11-minute walk from Portland Beach and 20 miles from Monkey World.

  • Breakfast options
    Review score
    Wonderful · 7 reviews

    Just a 4-minute walk from Portland Beach and 600 yards from Portland Castle, Pebbles Reach features accommodations in Portland with a garden.

  • Review score
    Exceptional · 53 reviews

    Seaview cottage with oodles of charm sleeps 4 is located in Portland, just 29 miles from Corfe Castle and a 11-minute walk from Portland Castle.

  • Breakfast options
    Review score
    Wonderful · 5 reviews

    The View offers accommodations in Portland, a few steps from Portland Beach and 4.8 miles from Weymouth Harbour. Free Wifi is provided throughout the property and private parking is available on site.

  • Review score
    Wonderful · 44 reviews

    Olympic Village Vela - Portland is located in Portland, just a 3-minute walk from Portland Beach and 20 miles from Monkey World.

These vacation rentals in Portland have options with FREE cancellation

  • Free cancellation options available
    Review score
    Wonderful · 47 reviews

    23 miles from Monkey World in Portland, Fishermans Cottage provides accommodations with access to a hot tub. Guests can benefit from a patio and a picnic area.

    Guest review
    Really lovely place with all you need and more for a lovely holiday 🙂 I would live there tomorrow if I could 👍 hot tub was lovely and the little lizard family in the rockery is brilliant nipping in and out in the sun! Loved it 👍
  • Free cancellation options available
    Review score
    Wonderful · 7 reviews

    Just a 3-minute walk from Portland Beach and 700 yards from Portland Castle, Osprey House Portland features accommodations in Portland with a garden.

  • Free cancellation options available
    Review score
    Wonderful · 8 reviews

    Cornerstone offers accommodations in Portland, a 7-minute walk from Portland Beach and 20 miles from Monkey World. This property offers access to a terrace and free private parking.

  • Free cancellation options available
    Review score
    Excellent · 553 reviews

    Just a 11-minute walk from Portland Beach and 400 yards from Portland Castle, Crabbers' Wharf features accommodations in Portland, with a terrace.

  • Free cancellation options available
    Review score
    Very Good · 6 reviews

    65 Ocean View is located in Portland, just 20 miles from Monkey World and 25 miles from Golden Cap.

  • Free cancellation options available
    Review score
    Excellent · 7 reviews

    The Blue Cottage offers accommodations in Portland, 29 miles from Corfe Castle and a 13-minute walk from Portland Castle.

  • Free cancellation options available
    Review score
    Excellent · 20 reviews

    SeaSky offers accommodations in Portland, a 4-minute walk from Portland Beach and 20 miles from Monkey World.

    Guest review
    Really nice property, very clean and well equipped. The communication with the host was very smooth.
  • Free cancellation options available
    Review score
    Excellent · 28 reviews

    Duke’s Cottage offers accommodations in Portland, 1.5 miles from Portland Beach and 22 miles from Monkey World. Featuring sea and garden views, this vacation home also includes free Wifi.

    Guest review
    Poppy & Sunny have made this place in to a dream! Loads of original features which are done to a very high standard. We loved our time at Dukes Cottage and cannot wait to visit again

Highly-rated vacation rentals in Portland

  • Review score
    Excellent · 94 reviews

    Just a 5-minute walk from Portland Beach and 0.6 miles from Portland Castle, Sea View Cottage in Dorset, Portland features accommodations in Portland, with a garden and a terrace.

  • 8.0+ review score
    Review score
    Very Good · 27 reviews

    Cozy Cove Chapel offers accommodations in Portland, 24 miles from Golden Cap and 28 miles from Corfe Castle.

    Guest review
    Really does live up to its name by being very cosy.
  • Review score
    Very Good · 18 reviews

    The Old Rope House in Portland offers accommodations with free Wifi, a 5-minute walk from Portland Beach, 20 miles from Monkey World, and 25 miles from Golden Cap.

  • 8.0+ review score
    Review score
    Very Good · 27 reviews

    Panoramic View is located in Portland, just a 10-minute walk from Portland Beach and 4.9 miles from Weymouth Harbour.

    Guest review
    Loved the light feel of the apartment from the balcony and the big glass balcony doors. Great views which were lovely to wake up to in the morning! The apartment had all the facilities you could need. Would definitely stay again.
  • 8.0+ review score
    Review score
    Excellent · 13 reviews

    22 miles from Monkey World in Portland, Pebble Reef features accommodations with access to a hot tub. With inner courtyard views, this accommodation provides a patio.

    Guest review
    The location was PERFECT. The four of us (two couples) had way more room than we needed and were easily able to walk to local grocery stores, hiking spots, rock climbing spots, and restaurants.
  • 8.0+ review score
    Review score
    Excellent · 7 reviews

    Olympic Cottage offers accommodations in Portland, 20 miles from Monkey World and 24 miles from Golden Cap. The 4-star vacation home is 4.6 miles from Weymouth Harbour.

  • 8.0+ review score
    Review score
    Excellent · 12 reviews

    Ammonite Cottage offers accommodations in Portland, 24 miles from Golden Cap and 28 miles from Corfe Castle. The 4-star vacation home is 20 miles from Monkey World.

    Guest review
    Lovely comfortable little cottage. Well placed in the island
  • Review score
    Excellent · 6 reviews

    Just a 6-minute walk from Portland Museum and half a mile from Rufus Castle, Nordor - lots of parking features accommodations in Portland with a garden.

FAQ about vacation rentals in Portland

Vacation Rentals That Guests Love in Portland

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  • Review score
    Excellent · 553 reviews
    Beautiful holiday home. Clean and spacious.
    Guest review by
    Beverley
    Family with young children
  • Review score
    Exceptional · 53 reviews
    Lovely location, Immaculately presented holiday home with all home comforts Particularly appreciated the 'little extra's' of welcome food hamper & fresh juice & milk left in the fridge & lovely view of sea/beach facing windows & lovely welcoming local pub just minutes away (Star inn)
    Guest review by
    Jason
    Group
  • Review score
    Excellent · 553 reviews
    Location was ideal for our purposes. We selected this property because it was something different from the usual holiday cottage. Impressed with the standard of furniture and fittings.
    Guest review by
    David
    Young couple

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