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Oxford holiday lettings
We found 719 holiday rentals — enter your dates for availability
If you'd like to stay close to Oxford, CT (OXC-Waterbury - Oxford), scroll through and discover private holiday rentals to choose your home away from home. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, which might include Wi-Fi and a fireplace. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Oxford, CT (OXC-Waterbury - Oxford)
Showing deals for:7 Nov - 14 Nov
Image gallery for Fabulous year round waterfront retreat on Lake Waramaug

1010 out of 10 rating
Exceptional
(6 reviews)
Fabulous year round waterfront retreat on Lake Waramaug
New Preston, CT
8% off
Price is £6,272
£6,272
£896 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

1010 out of 10 rating
Exceptional
(35 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is £3,079
£3,079
£440 per night
includes taxes & fees
Image gallery for Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

1010 out of 10 rating
Exceptional
(20 reviews)
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Danbury, CT
8% off
Price is £5,251
£5,251
£750 per night
includes taxes & fees
Image gallery for Historic Whitneyville Cottage

9.49.4 out of 10 rating
Exceptional
(16 reviews)
Historic Whitneyville Cottage
Hamden, CT
7% off
Price is £1,057
£1,057
£151 per night
includes taxes & fees
Image gallery for County Seat Colonial

1010 out of 10 rating
Exceptional
(11 reviews)
County Seat Colonial
Litchfield, CT
8% off
Price is £2,282
£2,282
£326 per night
includes taxes & fees
Image gallery for Lakefront Home, Close to Mt Southington!

1010 out of 10 rating
Exceptional
(19 reviews)
Lakefront Home, Close to Mt Southington!
Wolcott, CT
6% off
Price is £1,495
£1,495
£214 per night
includes taxes & fees
Image gallery for 100% WASHINGTON! PoshPadsCT "SENFF ESTATE"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ

1010 out of 10 rating
Exceptional
(16 reviews)
100% WASHINGTON! PoshPadsCT "SENFF ESTATE"8-BR, 2Hrs NYC, Heated Pool, Ski, BBQ
Washington, CT
17% off
Price is £11,646
£11,646
£1,664 per night
includes taxes & fees
Image gallery for Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video

1010 out of 10 rating
Exceptional
(21 reviews)
Beautiful Modern Architectural Home in Washington, Ct. 5 Star with video
Washington, CT
7% off
Price is £5,684
£5,684
£812 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is £6,402
£6,402
£915 per night
includes taxes & fees
Image gallery for Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball

1010 out of 10 rating
Exceptional
(5 reviews)
Candlewood Isle Cabin ~Dog-Friendly ~Lake Access~ Beach, Tennis, Basketball
New Fairfield, CT
14% off
Price is £2,097
£2,097
£300 per night
includes taxes & fees
Image gallery for 100% WASHINGTON! PoshPadsCT "SHEARER"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs

9.89.8 out of 10 rating
Exceptional
(11 reviews)
100% WASHINGTON! PoshPadsCT "SHEARER"2HrsNYC, 3BR, Heated Pool, Ski, BBQ, 2FPs
Washington, CT
34% off
Price is £4,201
£4,201
£600 per night
includes taxes & fees
Image gallery for Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups

1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful, Fun Lakefront Retreat -- Perfect for family reunions / groups
Brookfield, CT
16% off
Price is £9,780
£9,780
£1,397 per night
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes

1010 out of 10 rating
Exceptional
(11 reviews)
100% ROXBURY! PoshPadsCT "MOOSEHORN" 2HrsNYC, Mint 6-BR, Pool, Ski, BBQ, Bikes
Roxbury, CT
34% off
Price is £4,770
£4,770
£681 per night
includes taxes & fees
Image gallery for Candlewood Lake Perfection: Large and very private House, property and pool.

1010 out of 10 rating
Exceptional
(18 reviews)
Candlewood Lake Perfection: Large and very private House, property and pool.
Danbury, CT
8% off
Price is £12,335
£12,335
£1,762 per night
includes taxes & fees
Image gallery for Charming 1870 cape cottage in Litchfield

1010 out of 10 rating
Exceptional
(52 reviews)
Charming 1870 cape cottage in Litchfield
Litchfield, CT
8% off
Price is £1,505
£1,505
£215 per night
includes taxes & fees
Image gallery for 100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ

9.89.8 out of 10 rating
Exceptional
(6 reviews)
100% ROXBURY! PoshPadsCT "SENTRY HILL" 1.5Hrs NYC,Mint 6BR, Pool, Ski, Bike, BBQ
Roxbury, CT
51% off
Price is £3,387
£3,387
£484 per night
includes taxes & fees
Image gallery for Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

1010 out of 10 rating
Exceptional
(5 reviews)
Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub
New Milford, CT
12% off
Price is £3,727
£3,727
£532 per night
includes taxes & fees
Image gallery for Dove Haven | Find your Peace

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Dove Haven | Find your Peace
New Haven, CT
8% off
Price is £5,557
£5,557
£794 per night
includes taxes & fees
Image gallery for Luxury private beach front property

1010 out of 10 rating
Exceptional
(11 reviews)
Luxury private beach front property
Milford, CT
11% off
Price is £5,285
£5,285
£755 per night
includes taxes & fees
Image gallery for Best Town WASHINGTON! PoshPadsCT"51 SENFF" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!

9.49.4 out of 10 rating
Exceptional
(11 reviews)
Best Town WASHINGTON! PoshPadsCT"51 SENFF" 2Hrs-NYC Mint 5BR, Ski, BBQ, HotTub!
Washington, CT
34% off
Price is £4,729
£4,729
£676 per night
includes taxes & fees
Image gallery for Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!

1010 out of 10 rating
Exceptional
(12 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
7% off
Price is £1,706
£1,706
£244 per night
includes taxes & fees
Image gallery for Litchfield County Four Season Country Paradise

9.69.6 out of 10 rating
Exceptional
(46 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
8% off
Price is £6,282
£6,282
£897 per night
includes taxes & fees
Image gallery for 3br\2ba: Quiet and Cozy Getaway in Milford

1010 out of 10 rating
Exceptional
(6 reviews)
3br\2ba: Quiet and Cozy Getaway in Milford
Milford, CT
23% off
Price is £1,219
£1,219
£174 per night
includes taxes & fees
Image gallery for Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use

9.69.6 out of 10 rating
Exceptional
(71 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
8% off
Price is £1,388
£1,388
£198 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Villa
Chalet
Find the best place to stay - Oxford
Waterfront 3-bedroom house with AC and WiFi in tranquil Southbury
Sleeps 8 · 3 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
9 reviews(9 reviews)
Soak in the Lake Views at the Spacious Waterfront Apartment
Sleeps 8 · 4 bedrooms · 2+ bathrooms
STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit
Sleeps 10 · 3 bedrooms · 2+ bathrooms
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Private Apt in Southford-Southbury
Sleeps 2 · 1 bedroom · 1 bathroom
9.49.4 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Sunset Living
Sleeps 9 · 3 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Reunions at Candlewood Lake
Sleeps 8 · 4 bedrooms · 2+ bathrooms
3.03.0 out of 10
2 reviews(2 reviews)
Top rated rentals - Oxford
Super Stay in a lovely apartment
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
It's exactly as it appears on the site, a wonderful place, very tastefully decorated where every detail has been thought about to make your stay easy and highly enjoyable.Superb location too boot!
Tim C.
Stayed Mar 2025
Great stay and very helpful host
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
A quiet, cozy and lovely spot to stay for a guest from the UK. It was very easy to stay at Sharon's cottage. It was fairly well provided for with equipment and just very easy, comfortable and straightforward to stay in as a guest. Bed was very comfortable. Location-wise, like many American small towns, Woodbridge is very spread out, so shops have to be driven to, but there is a good farm shop down the road. Also a great area to go for walks nearby.
Stephanie B.
Stayed Mar 2025
Lovely House, Fabulous Lake Views
1010 out of 10
Exceptionalexceptional
88 reviews(88 reviews)
We thoroughly enjoyed our stay at Pinewood Retreat. Beds and linens were top quality, house had everything we needed, both indoors and out. Martha left clear instructions and was readily available at all times. A very pleasant stay.
Christiane L.
Stayed Jul 2024
Fabulous!
1010 out of 10
Exceptionalexceptional
121 reviews(121 reviews)
What a gem! Lovely cosy, relaxing feel in a stunning house. It made our once in a lifetime family holiday all the more special. The three year olds loved the space and being able to get to the beach in one minute.
Location was great with I 95 close by for easy access to all the attractions the area has to offer.
We all loved it.
Hilary P.
Stayed Aug 2023
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value