We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation rentals in Oakham

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Oakham

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Townhouse in Manton

4.99 out of 5 average rating, 129 reviews

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. There is a garden with a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included.

Cottage in Wing

4.88 out of 5 average rating, 243 reviews

Quiet Rural Chapel Conversion (Architectural Gem)

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside 2 min walk from King's Arms, Award winning Pub. Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

Condo in Tilton on the Hill

4.9 out of 5 average rating, 126 reviews

The Hayloft: Popular Hideaway - Sleeps 3.

After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

Cottage in Rutland

4.95 out of 5 average rating, 132 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

Cottage in Empingham

5 out of 5 average rating, 132 reviews

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, medical centre, hairdressing salon and pub just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Farm stay in Rutland

4.92 out of 5 average rating, 137 reviews

The Old Stables Retreat, Northfield Farm

Quiet, romantic retreat on small family-run working farm w. rare & native breed cattle & sheep. Fascinating place to learn about food & the countryside. Great place to stay & explore one of England's most lovely countryside areas. Farm shop, open for 20 + yrs, sells a wide range of home grown & home butchered meats & local flour, beers, ready meals & pies. Nr. Rutland Water, & Melton Mowbray, of pie fame, Stamford & Leicester. Great pubs abound, as do walks & entertainment of every kind.

Shepherd’s hut in Burton Lazars

4.99 out of 5 average rating, 143 reviews

Drift View Shepherds Hut

Welcome to Drift View, lovingly designed and built by ourselves and set on our family farm close to the Rutland/Leicestershire border. The hut is positioned in a private and secluded orchard, next to the farmyard and offers stunning views of the rural landscape. You can experience the peace and tranquillity the location provides whilst enjoying the luxury of the shepherds hut which has an en-suite with shower, fully equipped kitchen, double bed and both indoor/outdoor dining areas.

Condo in Uppingham

4.92 out of 5 average rating, 150 reviews

Comfy Modern APT - Sleeps 4

Located in the centre of the Historic Market Town of Uppingham. Based in is heart of the small county of Rutland. This apartment is a stones throw away to the gorgeous town centre, with markets every Friday, great places to eat and drink and some really cute little shops. A quick 10 minute drive to another Market Town of Oakham and not far from Rutland Water where you can enjoy some beautiful scenic walks. The apartment offers an allocated parking space and communal paved garden.

Home in Manton

4.95 out of 5 average rating, 243 reviews

Oak Tree Annexe

Oak Tree Annexe is set in a secluded and secure walled garden. You can park for free directly outside the house and will be staying in one of Rutland’s most desirable villages. Set on the fabulous cycle route around the water and with access to great walks directly from the house or a short drive away it’s a perfect location for exploring Rutland. Our village pub is a 3 minute stroll, serves food 7 days a week and offers our guests a 10% discount on their meals.

Townhouse in Rutland

4.95 out of 5 average rating, 284 reviews

Fennel House. Charming house in Oakham town centre

The townhouse is located on a quiet residential one way street. Oakham has stunning historical architecture, i.e a castle, quaint independent shops, pubs and restaurants are moments from the door. A short walk from the railway station. It is ideal for couples or families. A short drive is Rutland Water and is the largest man made lake in Europe 26 miles circumference and hosts many outdoor pursuits such as walking, cycling and bird watching.

Guest suite in Rutland

4.79 out of 5 average rating, 187 reviews

Self-contained Studio annexe in Oakham.

Lovely studio, has its own entrance at the front of house and access to back garden through the patio doors in the room. Recently added a shower in the studio so it is completely self contained now. Small kitchen area with sink and a full size fridge, and a washing machine if needed. There is one double bed in the studio, but also a self inflating single air bed with bedding if required. Smoking is not allowed throughout the property .

Barn in Whissendine

5 out of 5 average rating, 124 reviews

Beautiful Conversion in Rutland Countryside

Come and stay in our lovingly converted barn in the middle of the Rutland countryside. Perfect for a quiet get-away with lots of walking and cycling from the doorstep. Set in a 3 acre plot of our family home, you will have access to a private garden at the rear of the property plus our orchard should you wish to bring 1 small - medium sized dog with you. Unfortunately, the property is not suited to large dogs.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Hotels

Stylish accommodations and amenities

Popular amenities for Oakham vacation rentals

Free parking on premises

Air conditioning

Stay near Oakham's top sights

Oakham Castle19 locals recommend

The Lord Nelson17 locals recommend

The Admiral Hornblower16 locals recommend

The Grainstore Brewery & Tap12 locals recommend

Gates Garden Centre12 locals recommend

Hitchen's Barn11 locals recommend

Other great vacation rentals in Oakham

Cottage in Greetham

4.97 out of 5 average rating, 64 reviews

Halliday’s Cottage - Cosy Rutland Retreat

Home in Rutland

5 out of 5 average rating, 17 reviews

Field View

Cottage in Rutland

5 out of 5 average rating, 15 reviews

Hunky Dory Cottage

Condo in Uppingham

5 out of 5 average rating, 22 reviews

The Old Bookshop

Condo in Braunston

4.97 out of 5 average rating, 37 reviews

Healey House The Annex

Home in Edith Weston

5 out of 5 average rating, 17 reviews

4 * Cottage with Log Fire , Edith Weston

Home in Rutland

4.94 out of 5 average rating, 18 reviews

Rutland Lodge - Perfect Town Retreat

Rental unit in Rutland

4.92 out of 5 average rating, 50 reviews

The Limes - Beautiful Townhouse Apartment, Oakham

Quick stats about vacation rentals in Oakham

Total rentals
50 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Do house rentals in Oakham have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Oakham. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Oakham?
Make yourself at home in Oakham by choosing from our most frequently booked neighborhoods. We have over 110 vacation rentals in Braunston-in-Rutland, over 100 vacation rentals in Barleythorpe, and over 100 vacation rentals in Braunston.
Do house rentals in Oakham have free parking?
Absolutely! We offer over 20 house rentals with free parking in Oakham. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Oakham?
Yes! Work meets play with ease at over 20 vacation rentals in Oakham featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in house rentals in Oakham?
Experience the best of Oakham with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Oakham?
Four-legged friends are welcome in Oakham. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Oakham have wifi?
Absolutely! We offer over 20 house rentals with wifi in Oakham. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Oakham?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore