Vacation rentals in Oakham

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Top-rated vacation rentals in Oakham

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Guest favorite

Cottage in Wing

4.88 out of 5 average rating, 220 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

Apr 8 – 15

G$27,751 GYD per night

Guest favorite

Townhouse in Manton

4.99 out of 5 average rating, 100 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.

Jan 15 – 22

G$28,453 GYD per night

Guest favorite

Condo in Gretton

4.97 out of 5 average rating, 290 reviews

St James’s Cottage - Gretton

An independent, first floor, apartment in a 200yr old cottage. 1 bedroom available as superking bed or twin beds. Separate living room with kitchenette, combination microwave/oven/grill, single zone hob, toaster, kettle and full size fridge. Bathroom with shower. Free WiFi. Private, off road parking outside cottage. Secure garage space available upon request, for locking up bicycles, fishing tackle, golf clubs etc. Set in a lovely, quiet, village with two pubs & coffee shop in walking distance.

May 22 – 29

G$18,218 GYD per night

Guest favorite

Farm stay in Rutland

4.93 out of 5 average rating, 123 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.

Jun 6 – 13

G$28,639 GYD per night

Guest favorite

Cottage in Empingham

5.0 out of 5 average rating, 116 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.

Jan 23 – 30

G$35,375 GYD per night

Guest favorite

Cottage in Rutland

4.96 out of 5 average rating, 118 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, 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.

Jun 7 – 14

G$49,278 GYD per night

Guest favorite

Apartment in Rutland

4.89 out of 5 average rating, 206 reviews

Clock Cottage Self contained Rutland Rural Retreat

Clock Cottage is a self contained open plan suite located on the ground floor with garden views located within a characterful rural village within a 5 minute drive from Rutland water. The suite is open plan and includes a king sized bed, comfy living area and kitchen, Nespresso coffee machine, freestanding open plan bathtub and separate bathroom and outside dining area. The living area can be used as a family/friends bedroom with the use of a fold out sofa bed. Ideal for couples.

Oct 18 – 25

G$29,714 GYD per night

Guest favorite

Condo in Uppingham

4.92 out of 5 average rating, 118 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.

Mar 8 – 15

G$21,777 GYD per night

Guest favorite

Apartment in Stamford

4.96 out of 5 average rating, 558 reviews

Stamford Self Contained Flat Private Gated Parking

A private studio flat with kitchenette, bathroom and secure gated parking close to Stamford in Wothorpe. The flat is a 5 to 10 minute walk to the Town Center and the Train Station. Burghley Park is also very close and within walking distance (10-15 Minutes). Ideally placed for weekend breaks and weddings and for business travellers looking for easy access to transport routes like the A1 yet based close to the beautiful historic Stamford to take advantage of all that it offers.

Oct 10 – 17

G$22,052 GYD per night

Guest favorite

Townhouse in Rutland

4.95 out of 5 average rating, 250 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.

Sep 25 – Oct 2

G$31,562 GYD per night

Guest favorite

Guest suite in Rutland

4.8 out of 5 average rating, 117 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 .

Sep 30 – Oct 7

G$16,457 GYD per night

Guest favorite

Home in Manton

4.96 out of 5 average rating, 171 reviews

Oak Tree Annexe

This unique place has a style all of its own, set in a secluded and secure garden. The house is in one of Rutland’s most desirable villages and on the cycle route around the water offering easy access to all the activities that the area offers. The historic towns of Oakham and Uppingham are just a very short drive from the property. The village pub, which serves food, is a 2 minute walk and is very popular with visitors to the area.

Feb 4 – 11

G$27,471 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Oakham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Oakham's top sights

Oakham Castle19 locals recommend

Captain Noel Newton5 locals recommend

The Admiral Hornblower16 locals recommend

The Lord Nelson17 locals recommend

Lands' End3 locals recommend

Wheatsheaf3 locals recommend

Other great vacation rentals in Oakham

Guest favorite

Shepherd’s hut in Burton Lazars

5.0 out of 5 average rating, 105 reviews

Drift View Shepherds Hut

Sep 9 – 16

G$23,477 GYD per night

Guest favorite

Condo in Tilton on the Hill

4.89 out of 5 average rating, 114 reviews

The Hayloft: popular hideaway - sleeps 3

Sep 30 – Oct 7

G$29,628 GYD per night

Guest favorite

Condo in Northamptonshire

4.99 out of 5 average rating, 101 reviews

Tiny living at its best!

Apr 14 – 21

G$14,199 GYD per night

Superhost

Home in Rutland

4.8 out of 5 average rating, 142 reviews

Cherry Tree Cottage

Apr 9 – 16

G$20,604 GYD per night

Guest favorite

Home in Uppingham

4.93 out of 5 average rating, 106 reviews

36 High Street West -two bedroom luxury terrace

Aug 12 – 19

G$29,023 GYD per night

Guest favorite

Apartment in Ketton, Stamford, Lincs

4.94 out of 5 average rating, 295 reviews

Private Apartment in the Heart of Ketton, Stamford

Jun 6 – 13

G$22,772 GYD per night

Guest favorite

Cottage in Rutland

4.94 out of 5 average rating, 115 reviews

Daphne's cottage

Nov 28 – Dec 5

G$26,615 GYD per night

Guest favorite

Cottage in Duddington

4.99 out of 5 average rating, 211 reviews

Beautiful Grade II Listed Barn Conversion

Apr 18 – 25

G$27,548 GYD per night

Show all

Quick stats about vacation rentals in Oakham

Total rentals
40 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.2K reviews
Nightly prices starting at
G$8,342 GYD before taxes and fees

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 80 vacation rentals in Braunston, over 80 vacation rentals in Barleythorpe, and over 90 vacation rentals in Braunston-in-Rutland.
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 $40 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 a kitchen, over 20 homes with wifi, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Oakham

Top-rated vacation rentals in Oakham

Vacation rentals for every style

Houses

Cottages

Hotels

Popular amenities for Oakham vacation rentals

Stay near Oakham's top sights

Other great vacation rentals in Oakham

Shepherd’s hut in Burton Lazars

Condo in Tilton on the Hill

Condo in Northamptonshire

Home in Rutland

Home in Uppingham

Apartment in Ketton, Stamford, Lincs

Cottage in Rutland

Cottage in Duddington

Quick stats about vacation rentals in Oakham

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Oakham have a kitchen?

Where should I stay in Oakham?

Do house rentals in Oakham have free parking?

Are there vacation rentals with a dedicated workspace in Oakham?

How much does it cost to stay in house rentals in Oakham?

Are there pet-friendly vacation rentals in Oakham?

Do house rentals in Oakham have wifi?

What are the most popular amenities for House Rentals in Oakham?

Destinations to explore