Upwey Vacation Rentals from $175: Search Short-Term Rentals

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Our top choices for Upwey vacation rentals

A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

1. The Little Cottage

Weymouth

Lea

$642 nightly

Oct 27 - Oct 28

Total with taxes and fees

A bathroom with a window, a sink, and two potted plants.

2. Hardy View Farm House

Dorchester

Carol S.

$242 nightly

Oct 26 - Oct 27

Total with taxes and fees

A beach with people, a large striped tower, and buildings in the background.

3. The Sailors Studio|Sleeps2|Weymouth Beach|

Weymouth Town Center

$192 nightly

Oct 5 - Oct 6

Total with taxes and fees

A two-story house with a dark front door, a small porch, and a garage door.

4. Spacious, entire 3 bedroom house in Wool (The Purbecks)

Wool

A beach with a natural rock arch formation.

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool

Kristina

$363 nightly

Oct 11 - Oct 12

Total with taxes and fees

A coastal landscape with rocky cliffs, a sandy beach, and clear blue waters.

6. Comfy 2 bed house at Wareham train station; the ‘Gateway to the Purbecks’

Wareham

Luke E.

A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

7. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

$208 nightly

Oct 10 - Oct 11

Total with taxes and fees

A stone house with a thatched-roof extension, a stone well, and a grassy yard.

8. The Apple House at Moorbath Farm

Bridport

christopher b.

$232 nightly

Oct 7 - Oct 8

Total with taxes and fees

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

9. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

Winterborne Whitechurch

"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...

Stacia B.

$499 nightly

Oct 26 - Oct 27

Total with taxes and fees

A picnic table in a grassy area with a wooden fence and trees in the background.

10. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

$562 nightly

Oct 12 - Oct 13

Total with taxes and fees

A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

11. Sea Spray

Overcombe

$532 nightly

Oct 17 - Oct 18

Total with taxes and fees

A brick house with a sloped roof, a patio with a table and chairs, and a garden with various plants.

12. Battys Barn at Moorbath Farm

Bridport

James A.

$284 nightly

Oct 5 - Oct 6

Total with taxes and fees

A two-story house with a sloped roof, a front porch with chairs, and a small garden area.

13. Cosy country cottage for couples

BRIDPORT

Tracey H.

$307 nightly

Oct 5 - Oct 6

Total with taxes and fees

A living room with a blue sofa, a yellow rug, a wooden cabinet, and a TV on the wall.

14. Beautiful newly refurbished annexe 2 miles from Wareham Quay

Sandford

$171 nightly

Nov 3 - Nov 4

Total with taxes and fees

15. Hide-a-way

Weymouth

Kim

$458 nightly

Oct 7 - Oct 8

Total with taxes and fees

A cozy room with a stone wall, a fireplace, a sofa, and a window.

16. Norden Cottage

Weymouth

"The cottage itself is lovely, and has a lot of potential. It’s a large cottage which accomodates 5. Lighting wasn’t working in all rooms which was a nuisance and the facilities in the kitchen were dirty and not maintained well. Oven and stove worked, coffee machine filthy. Given that you would hire a cottage to do self catering, it wasn’t one of the better cottages we have stayed in. We found it a cold welcoming, no welcome note, only a small box of biscuits on entry. Cottage was really...

Hilary

$649 nightly

Oct 17 - Oct 18

Total with taxes and fees

A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

17. 2 Bathsheba Terrace

Dorchester

Rachael

$486 nightly

Oct 13 - Oct 14

Total with taxes and fees

A traditional stone building with a thatched roof, a small window, and a sign prohibiting parking on the grass.

18. Badgers Cottage

Weymouth

Neil

$575 nightly

Oct 9 - Oct 10

Total with taxes and fees

A modern kitchen with a dining area, featuring a large window, a microwave, and a sink.

19. Coastguard Lookout

Wyke Regis

$504 nightly

Oct 10 - Oct 11

Total with taxes and fees

A wooden deck with a pergola, a table with chairs, and a brick pathway.

20. Home Waters

Wyke Regis

$684 nightly

Oct 31 - Nov 1

Total with taxes and fees

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Top Upwey Hotel Reviews

The Frampton Arms

10/10 Excellent

"We stayed here for a local wedding. Staff were very friendly and accommodating. Lovely food in the evening. Very nice rooms with comfy beds and a good shower."

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"Even though the room was very warm I still had an amazing time. Previously when we have been to Weymouth for a short break we stay at the Premier Inn. This was definitely alot better, and the staff so much friendlier and I could open the window alot wider, so during the evening and night you could hear the waves crashing onto the shore. Just cross the road and you're on the beach. Its within walking distance to the shops. We stayed for 3 nights so ate there in the evening. I can recommend the rack of ribs, but all of the food was amazing, and reasonably priced. There's alot going on each evening, as well as during the day. Already thinking about booking for next year again."

Fairhaven Hotel

10/10 Excellent

"Corridors have sensor lights, some of which take a while to light up so it can be dark. Housekeeping was fab with clean towels and refreshments replaced every day. Excellent beach front location. Our room this time was on the 2nd floor with a lovely bay window. We have also stayed in the 1st floor room directly below, both are great rooms. Car parking was heavily discounted at an excellent price."

Belhuish Farmhouse

10/10 Excellent

"This property is unique and rare - owned by an innkeeper who welcomes you to his table with warm hospitality and decades of history to share. Mr. Miller is a wealth of information and retired thatcher. This is not a place for you if you need a well-appointed hotel to feel good about leaving your home. This is a historic property with purbeck flag stones and Welsh slate on the kitchen floor. The stove is as wide as your arms. There are wild pheasants in the fields and silent nights nestled in a hidden valley a bit off the main road. This a place where ruins of the past sit on the land beside a welcoming farmhouse. Great for introverts, writers, couples, families, and solo travelers. Backpackers will love it."

Find out more about Upwey

Everything you need to know about Upwey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upwey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upwey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upwey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upwey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Upwey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $175 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upwey rentals

At Expedia, we put the best Upwey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upwey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upwey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upwey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Upwey?

Yes, we offer vacation rentals near well known points of interest in Upwey, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Upwey has to offer?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: Visitors like this Upwey vacation home rental. It comes with WiFi so you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Upwey?

While exploring the area, visit family-friendly sights like Abbotsbury Swannery, or get outside and enjoy nature at Dorset National Landscape. In the larger area, you’ll find Lodmoor Country Park and Bowleaze Cove Beach.

What’s a vacation rental in Upwey like?

Vacation rentals are private properties you can book for a long or short time in Upwey. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for families.

Room 1

Check prices for these dates

Our top choices for Upwey vacation rentals

1. The Little Cottage

2. Hardy View Farm House

3. The Sailors Studio|Sleeps2|Weymouth Beach|

4. Spacious, entire 3 bedroom house in Wool (The Purbecks)

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

6. Comfy 2 bed house at Wareham train station; the ‘Gateway to the Purbecks’

7. 1 bedroom accommodation in Ibberton, Blandford Forum

8. The Apple House at Moorbath Farm

9. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

10. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

11. Sea Spray

12. Battys Barn at Moorbath Farm

13. Cosy country cottage for couples

14. Beautiful newly refurbished annexe 2 miles from Wareham Quay

15. Hide-a-way

16. Norden Cottage

17. 2 Bathsheba Terrace

18. Badgers Cottage

19. Coastguard Lookout

20. Home Waters

Find vacation rentals that suit your style

Top Upwey Hotel Reviews

The Frampton Arms

The Jubilee Hotel West- with Spa Facilities

Fairhaven Hotel

Crown Hotel

The Jubilee Hotel East- with Spa Facilities

Kingston Country Courtyard

Belhuish Farmhouse

Sleeping Bear Hotel Dorchester

The Bull Hotel

Find out more about Upwey

Frequently asked questions