A red barn with a green roof, surrounded by a grassy field and leafless trees.

Orwell Vacation Rentals

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Orwell vacation rentals

A two-story house with a front porch, a small garden, and a wooden deck.

1. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (100 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
$229 nightly
The price is $229
Oct 24 - Oct 25
Total with taxes and fees
Little house on the farm
A rustic kitchen with wooden beams, a central island, bar stools, and a dining table with placemats.

2. 3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Rome
10.0 out of 10, Exceptional, (61 reviews)
"Folks this cabin is amazing! Rustic in design, modern in amenities and so very comfortable. Exceptional detail was paid to decor and quality furnishings which round out one of the nicest VRBO I've stayed at."
United States
Amy P.
$225 nightly
The price is $235
Oct 26 - Oct 27
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
A staircase leading to a kitchen with dark wooden cabinets and a stainless steel refrigerator.

3. Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (11 reviews)
"Very nice people. Everything is very fresh, new and very well decorated."
United States
Kelly G.
$229 nightly
The price is $229
Oct 24 - Oct 25
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
A covered porch with wicker chairs and a blue patterned rug.

4. 2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
8.6 out of 10, Excellent, (7 reviews)
"Fantastic clean and easy perfect for our quick trip!"
United States
Ashley B.
$188 nightly
The price is $188
Oct 22 - Oct 23
Total with taxes and fees
2 bedroom apartment in the beautiful Middlefield countryside!
A living room with a brown leather sofa, two armchairs, a small table with a lamp, and a striped rug.

5. Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Warren
10.0 out of 10, Exceptional, (142 reviews)
"The house was perfect for our stay and was exactly as described!"
United States
Michael R.
$172 nightly
The price is $172
Oct 22 - Oct 23
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
A cabin with a deck, two lounge chairs, and a small table.

6. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely a lovely place to stay! Felt like home from the minute we walked in the door. The owners amazing cookies are to die for!!! Would love to go back and stay again!"
United States
Amy M.
$229 nightly
The price is $229
Oct 22 - Oct 23
Total with taxes and fees
Tiny Haven
A white brick building with a blue door and a 'WELCOME' sign. There is a small round table with a potted plant and two red metal chairs.

7. White Brick Inn in Pymatuning National Park

White Brick Inn in Pymatuning National Park
Jamestown
9.8 out of 10, Exceptional, (149 reviews)
"Super cute, clean, and was the perfect location for our needs"
United States
Tabitha W.
$120 nightly
The price is $132
Oct 22 - Oct 23
Total with taxes and fees
White Brick Inn in Pymatuning National Park
A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

8. Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (72 reviews)
"Really nice place to stay."
United States
Phillip
$162 nightly
The price is $162
Oct 27 - Oct 28
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A square fire pit table with two metal chairs on a wooden deck.

9. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay :) "
United States
Jennifer S.
$165 nightly
The price is $169
Oct 30 - Oct 31
Total with taxes and fees
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A compact kitchen with a sink, stove, microwave, and cabinets.

10. Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.

Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.
Cortland
9.8 out of 10, Exceptional, (7 reviews)
"My wife’s in rehab in Warren and hopefully can recheck back in with returning customer discount.!"
United States
Robert K.
$129 nightly
The price is $133
Oct 26 - Oct 27
Total with taxes and fees
Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.
A wooden treehouse with a balcony and a ladder, surrounded by a forest.

11. Cabin in the woods. Minutes to Pymatuning Lake.

Cabin in the woods. Minutes to Pymatuning Lake.
Williamsfield
9.6 out of 10, Exceptional, (48 reviews)
"Thank you Maggie you are a great host, we had a wonderful time the kids loved fishing, your awesome property is amazing"
United States
Ivy
$184 nightly
The price is $190
Oct 31 - Nov 1
Total with taxes and fees
Cabin in the woods. Minutes to Pymatuning Lake.
A bedroom with a wooden ceiling, a bed with a wooden headboard, a blue chair, a bench, and a cowhide rug.

12. Romantic Woodside Cabin | Hot Tub & Fire Pit

Romantic Woodside Cabin | Hot Tub & Fire Pit
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
$182 nightly
The price is $201
Nov 4 - Nov 5
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

13. A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (49 reviews)
"The house was clean, well furnished, and comfortable. Anthony was in contact and available if needed. We enjoyed our visit very much."
United States
Nancy M.
$199 nightly
The price is $199
Oct 22 - Oct 23
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A hallway with a wooden floor, a staircase with a purple railing, and a door leading to a kitchen area.

14. Peaceful 3-bedroom house near the lake

Peaceful 3-bedroom house near the lake
Andover
10.0 out of 10, Exceptional, (10 reviews)
"The house is very nice, clean, close to a lot of things, and booking was easy. A place you could stay all year round at a good price."
United States
Susie W.
$297 nightly
The price is $297
Oct 25 - Oct 26
Total with taxes and fees
Peaceful 3-bedroom house near the lake
A house with a dark exterior, a yellow door, a small porch, and a garden with various plants.

15. Private, Quiet, 1 BR 1 Bath Chardon Guesthouse w AC

Private, Quiet, 1 BR 1 Bath Chardon Guesthouse w AC
Chardon
10.0 out of 10, Exceptional, (1 review)
"Flawless. They thought of everything that would make our stay so good you begin to think about when your next visit will be. The property was private and an oasis. Outside was a beautiful setting. The inside was super clean and very comfortable and felt like home. Very relaxing. We were in town for a very busy wedding. To have this as our base of operation was fantastic. The owners are exceptional people. Top tier! Thank you!"
United States
Russell J.
$210 nightly
The price is $210
Nov 21 - Nov 22
Total with taxes and fees
Private, Quiet, 1 BR 1 Bath Chardon Guesthouse w AC
A white building with a black door and a visible window.

16. Cozy 2-bedroom apartment in welcoming Cortland with AC

Cozy 2-bedroom apartment in welcoming Cortland with AC
Cortland
$170 nightly
The price is $170
Oct 22 - Oct 23
Total with taxes and fees
Cozy 2-bedroom apartment in welcoming Cortland with AC
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

17. Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Geneva
9.6 out of 10, Exceptional, (44 reviews)
"Nice place for a weekend. Good price and everything we needed"
United States
Devan M.
$196 nightly
The price is $196
Oct 22 - Oct 23
Total with taxes and fees
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
A compact kitchen with a microwave, stove, sink, and refrigerator.

18. Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Geneva
9.4 out of 10, Exceptional, (27 reviews)
"Super comfy bed, A/C was excellent, cute little 50’s style restaurant just down the road. "
United States
Stephanie
$200 nightly
The price is $209
Oct 22 - Oct 23
Total with taxes and fees
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
A large, two-story house with a prominent front porch, a visible garage, and a small attached structure.

19. Cozy One Room Studio in Wine Country!

Cozy One Room Studio in Wine Country!
Jefferson
10.0 out of 10, Exceptional, (1 review)
"This property is remote- there are attractions within a half hour drive, so if you’re hoping to walk to nearby places, this isn’t the one. Everything is much higher quality than I typically see in a VRBO rental. The bed was so comfy I didn’t want to get up! The shower is nice and the couple who own the house are very nice and accommodating "
United States
Jessica B.
$238 nightly
The price is $241
Oct 24 - Oct 25
Total with taxes and fees
Cozy One Room Studio in Wine Country!
A living room with a flat-screen TV mounted on the wall, a dark wood fireplace, and a brown leather sofa.

20. Quaint recently renovated apartment with AC in Geneva close to lake and wineries

Quaint recently renovated apartment with AC in Geneva close to lake and wineries
Geneva
9.8 out of 10, Exceptional, (7 reviews)
"For a last minute stay for a big event, it was just what we need it. It was a little small but it had everything we would have wanted for the price."
United States
Donna G.
$188 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
Quaint recently renovated apartment with AC in Geneva close to lake and wineries
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Orwell Hotel Reviews

Hampton Inn Madison

Hampton Inn Madison

8/10 Good
"Clean. Pillows terrible. It’s perfectly acceptable. Nothing more. They should list that restaurant only open 4 nights- Wed thru Sat."
Lauren 1-night trip
Posted 4 hours ago
Hampton Inn Madison

Find out more about Orwell

Everything you need to know about Orwell 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 Orwell 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 Orwell vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Orwell vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orwell. 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 Orwell 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 $132 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 Orwell rentals

At Expedia, we put the best Orwell 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 Orwell 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 Orwell 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 Orwell. 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 Orwell?

Yes, there are vacation rentals close to top local attractions in Orwell, or you can choose a more remote option if you want a relaxing place to stay.

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

FISHING AND FAMILY FRIENDLY- NOTHING FANCY: This vacation home rental near Orwell is located in a rural location and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Orwell?

While exploring the area, visit family-friendly sights like Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Hogback Ridge. Middlefield Village Center and Geauga County Fairgrounds are a couple of places you'll find in the larger area.

What’s a vacation rental in Orwell like?

A vacation rental is a private property you can book for several days or longer in Orwell. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.