Windsor Holiday Rentals from €165: Search Short-Term Rentals

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Our top choices for Windsor holiday rentals

A bathroom with a white sink, wooden paneling, a mirror with a bead trim, and a view of a house through a window.

1. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

Hallowell

Anthony R.

includes taxes & fees

21 Oct - 22 Oct

A living room with a fireplace, a glass of white wine, a cutting board with cheese, and a remote control.

2. High End Apartment in Downtown Hallowell

Hallowell

Shawn

includes taxes & fees

16 Nov - 17 Nov

A wooden cabin with a porch, a door, and a green chair.

3. Sister A-Frame in Woods B

Oakland

Amanda M.

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a front porch, a small tree, and a brick pathway.

4. Perfectly Located 1 Bedroom, newly remodeled

Augusta

"The area is so convenient for any business you have in the Augusta area- right off the main thoroughfare yet far enough away to be private. Check in was as simple as getting the lock code from vrbo check in emails. The apartment is even more lovely than the pictures- almost too clean and comfortable to be real! Bedtime was silent so I got a great night sleep. I only wish we would have had more time to enjoy :) Highly recommend!! "

w c.

A modern living room with a flat-screen TV, a yellow armchair, a beige sofa, and a coffee table.

5. Two bedroom Mid Century Modern apartment in Downtown Hallowell

Hallowell

Melissa F.

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a bed, a bedside table, a lamp, and a window with curtains.

6. The heart of the Belgrade Lakes

Oakland

"It was amazing! Shawna was great! I forgot to add our pet on the original booking and she was so responsive and we got everything sorted out. The apartment was so comfortable and decorated beautifully! Great space from kids room with things to entertain them to calm adult bedroom. The kitchen was well stocked and had everything you could think of. We loved “the fluffy butt hut” chicken coop!!! This is a dream place, from veggie garden, pool, tree house, chicken coop. Love it! Will definitely...

Tri C.

includes taxes & fees

21 Oct - 22 Oct

A wooden deck with picnic tables overlooking a calm lake, surrounded by dense greenery.

7. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

West Gardiner

Lisa W.

includes taxes & fees

21 Oct - 22 Oct

A wooden deck with a glass door leading to a room.

8. Tiny Cottage Near Everything 10

Edgecomb

Gene

includes taxes & fees

21 Oct - 22 Oct

A living room with a fireplace, a mounted TV, and bookshelves filled with books.

9. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

Nobleboro

Rhiannon A.

includes taxes & fees

21 Oct - 22 Oct

A covered porch with wicker furniture, a white door, and a welcome mat.

10. Cozy cottage in the Winthrop Lakes Area

Winthrop

Treseanne A.

includes taxes & fees

5 Nov - 6 Nov

11. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

Waldoboro

includes taxes & fees

21 Oct - 22 Oct

12. Central Maine Apartment offering 4 Seasons of Fun.

Oakland

kathy e.

includes taxes & fees

1 Nov - 2 Nov

A deck with two Adirondack chairs, a metal fire pit, and a view of a lake surrounded by trees.

13. China Lake, Dog Friendly, Lots of space for family gatherings

China

Lisa J.

A living room with a sectional sofa, a coffee table, and a patterned rug. There are two paintings on the walls, a lamp, and a potted plant.

14. Cozy House in the heart of Waterville Maine.

Waterville

Leslie G.

includes taxes & fees

2 Nov - 3 Nov

A spacious room with a wooden floor, a striped rug, a black chair, and a dining table.

15. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

Winthrop

Laura M.

includes taxes & fees

21 Oct - 22 Oct

A wooden cabin with a porch, a rocking chair, and a table with a lantern.

16. Naughty Dog Private Island Log Cabin

Monmouth

"Honestly, this property and the whole experience exceeded all my expectations (which were already pretty high). Kent and the team were so accommodating, making sure that we had everything that we needed and were available at any time. They made special plans to accommodate some friends for a day visit and were so kind and helpful. The property itself was so perfect for what we wanted and the dog so enjoyed the freedom that only a private island can bring! Thanks, Kent, for a very memorable stay....

Peter O.

includes taxes & fees

1 Nov - 2 Nov

A wooden interior with a radial wooden ceiling design and a central skylight.

17. Island Tree House Glamping

Monmouth

Desiree L.

includes taxes & fees

28 Oct - 29 Oct

A bedroom with a bed, a bedside table, and a window with curtains.

18. Peaceful Intown Studio ~ Walk to Shops & Dining

Newcastle

Brian

includes taxes & fees

31 Oct - 1 Nov

A modern living room with a large window, a wooden ceiling, and a view of a green landscape.

19. Come Spring Farm Airstream , Lake & farm animals

Union

Thomas W.

A spacious tent with a large skylight, a bed, a sofa, a lamp, and a fireplace.

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Union

Sabrina D.

includes taxes & fees

23 Oct - 24 Oct

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Top Windsor Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent

"Good stay"

Cod Cove Inn, BW Signature Collection

10/10 Excellent

"It was an excellent stay. The staff was wonderful. She got us a room on the ground floor and it's a motel style entrance, so we just rolled our bags right into the room, which is always cool and definitely helps since taking them upstairs would've been pretty hard. Breakfast was OK, like all the other hotels of this level. The beds were cozy, the room was warm, all was well."

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as €165 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 Windsor 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 Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. 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

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay. Windsor is known for its shopping and restaurants.

What are some of the best holiday rentals that Windsor has to offer?

Warm & Inviting Lakeside Retreat, Private, Tranquil Picture Perfect Setting: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Wiscasset, Waterville and Farmington Railway Museum, or get outside and enjoy nature at Threemile Pond. In the wider area, you’ll find Capitol Park and Maine State House.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.

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Treat yourself

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Check prices for these dates

Our top choices for Windsor holiday rentals

1. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

2. High End Apartment in Downtown Hallowell

3. Sister A-Frame in Woods B

4. Perfectly Located 1 Bedroom, newly remodeled

5. Two bedroom Mid Century Modern apartment in Downtown Hallowell

6. The heart of the Belgrade Lakes

7. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

8. Tiny Cottage Near Everything 10

9. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10. Cozy cottage in the Winthrop Lakes Area

11. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

12. Central Maine Apartment offering 4 Seasons of Fun.

13. China Lake, Dog Friendly, Lots of space for family gatherings

14. Cozy House in the heart of Waterville Maine.

15. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

16. Naughty Dog Private Island Log Cabin

17. Island Tree House Glamping

18. Peaceful Intown Studio ~ Walk to Shops & Dining

19. Come Spring Farm Airstream , Lake & farm animals

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Cod Cove Inn, BW Signature Collection

Best Western Plus Augusta Civic Center Inn

Lockwood Hotel

Super 8 by Wyndham Augusta

Comfort Inn Augusta

Senator Inn & Spa

Best Western Plus Waterville Grand Hotel

Days Inn by Wyndham Augusta

Find out more about Windsor

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Windsor

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Windsor holiday rentals

1. River View Retreat, Hot Tub, Balcony, Kayaks & Bikes

2. High End Apartment in Downtown Hallowell

3. Sister A-Frame in Woods B

4. Perfectly Located 1 Bedroom, newly remodeled

5. Two bedroom Mid Century Modern apartment in Downtown Hallowell

6. The heart of the Belgrade Lakes

7. Maine river escape: free kayaks, paddle boards, tennis, cute rabbits and fun!

8. Tiny Cottage Near Everything 10

9. “Otter Getaway” Cozy Damariscotta Lake Year Round Cottage

10. Cozy cottage in the Winthrop Lakes Area

11. Applecroft Cabin No. 3 - Modern off-grid cabin deep in the woods.

12. Central Maine Apartment offering 4 Seasons of Fun.

13. China Lake, Dog Friendly, Lots of space for family gatherings

14. Cozy House in the heart of Waterville Maine.

15. Jill's Place, new construction, lake access Cobbosee, 1 mile from Cabin Masters

16. Naughty Dog Private Island Log Cabin

17. Island Tree House Glamping

18. Peaceful Intown Studio ~ Walk to Shops & Dining

19. Come Spring Farm Airstream , Lake & farm animals

20. Dome 3 at Come Spring Farm Glamping - Alpaca Farm

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Maine Evergreen Hotel, an Ascend Collection Hotel

Find out more about Windsor

Frequently asked questions

Go further with the Expedia app