Vacation rentals in Middlesex County, CT

Best vacation rentals and Airbnb offers in Middlesex County, CT

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Apartment, Middlesex County

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes. is a apartment in Middlesex County. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Beautuful, private studio apartment with access to hiking trails, kayaks, bikes.

Beautuful, private studio apartment with access to hiking trails, kayaks, bikes. is a apartment in Middlesex County. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $951.

From$136/night

Show›

East Haddam CT Country Loft

Holiday Home, Middlesex County

East Haddam CT Country Loft is a holiday home in Middlesex County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About East Haddam CT Country Loft

East Haddam CT Country Loft is a holiday home in Middlesex County, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,457.

From$162/night

Show›

Lovely Cottage by Lake Hayward

Cottage, Middlesex County

Lovely Cottage by Lake Hayward is a cottage in Middlesex County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

Read more

About Lovely Cottage by Lake Hayward

Lovely Cottage by Lake Hayward is a cottage in Middlesex County, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,240.

From$177/night

Show›

Life on the Farm

Apartment, Middlesex County

Life on the Farm is a apartment in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Life on the Farm

Life on the Farm is a apartment in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,278.

From$183/night

Show›

Vacation rentals with a pool in Middlesex County, CT

Add a pool to the search when you want an easy place to cool off between outings.

The Bevin House B&B

B & B, Middlesex County

The Bevin House B&B is a b & b in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with…

Read more

About The Bevin House B&B

The Bevin House B&B is a b & b in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,064.

From$266/night

Show›

The Bevin House Bed & Breakfast

B & B, Middlesex County

The Bevin House Bed & Breakfast is a b & b in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

Read more

About The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast is a b & b in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,098.

From$270/night

Show›

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Holiday Home, Middlesex County

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston is a holiday home in Middlesex County, with pool access, kitchen access, and a quieter setting. This stay gives…

Read more

About Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston is a holiday home in Middlesex County, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $5,448.

From$778/night

Show›

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

Villa, Middlesex County

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond is a villa in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond

Luxury Riverfront Estate - Pool, Spa, Tennis, & Pond is a villa in Middlesex County, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $9,647.

From$1,378/night

Show›

Vacation rentals with parking in Middlesex County, CT

Find vacation rentals that make arriving by car easier.

Charming In-Law Apt with independant entrance in Guilford

Holiday Home, Middlesex County

Charming In-Law Apt with independant entrance in Guilford is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring…

Read more

About Charming In-Law Apt with independant entrance in Guilford

Charming In-Law Apt with independant entrance in Guilford is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,263.

From$180/night

Show›

Cozy basement apartment with private bathroom, kitchen and entrance.

Holiday Home, Middlesex County

Cozy basement apartment with private bathroom, kitchen and entrance. is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for…

Read more

About Cozy basement apartment with private bathroom, kitchen and entrance.

Cozy basement apartment with private bathroom, kitchen and entrance. is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,615.

From$231/night

Show›

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach

Cottage, Middlesex County

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach is a cottage in Middlesex County, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach

Vintage Cottage- 2 Bedrooms, Sleeps 6 Comfortably, Chalker Beach is a cottage in Middlesex County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,799.

From$257/night

Show›

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Apartment, Middlesex County

Private 2nd-Floor Apt · 4 Mins to Beach · EV Charger & Parking Included is a apartment in Middlesex County, with easy beach access, parking, and kitchen access. This stay gives travelers a…

Read more

About Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt · 4 Mins to Beach · EV Charger & Parking Included is a apartment in Middlesex County, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,817.

From$260/night

Show›

Pet-friendly vacation rentals in Middlesex County, CT

Bring your pet along with stays that welcome four-legged travelers.

Cozy newly remodeled home close to major amenities in Connecticut a

Holiday Home, Middlesex County

Cozy newly remodeled home close to major amenities in Connecticut a is a holiday home in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a…

Read more

About Cozy newly remodeled home close to major amenities in Connecticut a

Cozy newly remodeled home close to major amenities in Connecticut a is a holiday home in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,585.

From$226/night

Show›

#24 *Serenity* A Lakefront Cottage Retreat

Holiday Home, Middlesex County

#24 *Serenity* A Lakefront Cottage Retreat is a holiday home in Middlesex County, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable…

Read more

About #24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat is a holiday home in Middlesex County, with pet-friendly space, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,752.

From$250/night

Show›

3 BR Apartment Near Wesleyan 201

Apartment, Middlesex County

3 BR Apartment Near Wesleyan 201 is a apartment in Middlesex County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About 3 BR Apartment Near Wesleyan 201

3 BR Apartment Near Wesleyan 201 is a apartment in Middlesex County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,872.

From$267/night

Show›

Peace Barn in the heart of the CT River Valley

Holiday Home, Middlesex County

Peace Barn in the heart of the CT River Valley is a holiday home in Middlesex County, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing…

Read more

About Peace Barn in the heart of the CT River Valley

Peace Barn in the heart of the CT River Valley is a holiday home in Middlesex County, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, internet, and non smoking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,967.

From$424/night

Show›

Vacation rentals with a kitchen in Middlesex County, CT

Compare stays with kitchen access for longer trips and easier meals.

Guilford home -self check in, off-street parking

Holiday Home, Middlesex County

Guilford home -self check in, off-street parking is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Guilford home -self check in, off-street parking

Guilford home -self check in, off-street parking is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,752.

From$250/night

Show›

3 BR Apartment Near Wesleyan 202

Apartment, Middlesex County

3 BR Apartment Near Wesleyan 202 is a apartment in Middlesex County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202 is a apartment in Middlesex County, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,173.

From$310/night

Show›

Family Friendly, Beach Themed Cottage - Chalker Beach

Cottage, Middlesex County

Family Friendly, Beach Themed Cottage - Chalker Beach is a cottage in Middlesex County, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable…

Read more

About Family Friendly, Beach Themed Cottage - Chalker Beach

Family Friendly, Beach Themed Cottage - Chalker Beach is a cottage in Middlesex County, with easy beach access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,208.

From$315/night

Show›

Gorgeous Lakehouse with Handicap Accessibiliy

Holiday Home, Middlesex County

Gorgeous Lakehouse with Handicap Accessibiliy is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

Read more

About Gorgeous Lakehouse with Handicap Accessibiliy

Gorgeous Lakehouse with Handicap Accessibiliy is a holiday home in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,276.

From$468/night

Show›

Family-friendly vacation rentals in Middlesex County, CT

Plan a trip with stays that give families more room to spread out.

Tiny Lakefront Cottage!

Apartment, Middlesex County

Tiny Lakefront Cottage! is a apartment in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings,…

Read more

About Tiny Lakefront Cottage!

Tiny Lakefront Cottage! is a apartment in Middlesex County, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,335.

From$191/night

Show›

Saybrook Point Cottage - Charming and Private

Cottage, Middlesex County

Saybrook Point Cottage - Charming and Private is a cottage in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

Read more

About Saybrook Point Cottage - Charming and Private

Saybrook Point Cottage - Charming and Private is a cottage in Middlesex County, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,543.

From$220/night

Show›

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Cottage, Middlesex County

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! is a cottage in Middlesex County, with pet-friendly space, kitchen access, and room for a group. This stay gives…

Read more

About Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! is a cottage in Middlesex County, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,626.

From$232/night

Show›

Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

Cottage, Middlesex County

Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private. is a cottage in Middlesex County, with parking, kitchen access, and a quieter setting. This stay gives…

Read more

About Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private.

Lovely, cozy Cottage on a non working farm in a rural town. Quiet and private. is a cottage in Middlesex County, with parking, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,227.

From$318/night

Show›