Vacation rentals in Portland, CT

62 available vacation rental offers

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Best vacation rentals and Airbnb offers in Portland, CT

Seasons Hospitality offers all new 1Br with tons of charm - Portland, CT

Seasons Hospitality offers all new 1Br with tons of charm

Apartment, Portland

Seasons Hospitality offers all new 1Br with tons of charm is a apartment in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Seasons Hospitality offers all new 1Br with tons of charm

Seasons Hospitality offers all new 1Br with tons of charm is a apartment in Portland, with parking, 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, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,042.

From$149/night
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Chic Suite with Recliner - Webster Hill Suite 1W - Portland, CT

Chic Suite with Recliner - Webster Hill Suite 1W

Apartment, Portland

Chic Suite with Recliner - Webster Hill Suite 1W is a apartment in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chic Suite with Recliner - Webster Hill Suite 1W

Chic Suite with Recliner - Webster Hill Suite 1W is a apartment in Portland, 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 $1,110.

From$159/night
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East Haddam CT Country Loft - Portland, CT

East Haddam CT Country Loft

Holiday Home, Portland

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

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About East Haddam CT Country Loft

East Haddam CT Country Loft is a holiday home in Portland, 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
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Cozy and stylish apartment in central meriden - Portland, CT

Cozy and stylish apartment in central meriden

Holiday Home, Portland

Cozy and stylish apartment in central meriden is a holiday home in Portland, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Cozy and stylish apartment in central meriden

Cozy and stylish apartment in central meriden is a holiday home in Portland, 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 $1,211.

From$173/night
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Vacation rentals with a pool in Portland, CT

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

The Bevin House B&B - Portland, CT

The Bevin House B&B

B & B, Portland

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

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About The Bevin House B&B

The Bevin House B&B is a b & b in Portland, 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
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The Bevin House Bed & Breakfast - Portland, CT

The Bevin House Bed & Breakfast

B & B, Portland

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

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About The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast is a b & b in Portland, 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
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Home away from home Hot Tub and Pool in Middletown home of Wesleyan university - Portland, CT

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Holiday Home, Portland

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university is a holiday home in Portland, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university is a holiday home in Portland, with pool access 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, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,160.

From$594/night
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Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston - Portland, CT

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

Holiday Home, Portland

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

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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 Portland, 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
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Vacation rentals with parking in Portland, CT

Find vacation rentals that make arriving by car easier.

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!! - Portland, CT

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!!

Apartment, Portland

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!! is a apartment in Portland, with parking, room for a group, and a quieter setting. This stay gives travelers…

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About Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!!

Spacious 3-Bedroom Home Awaits 2nd Floor - Designed for Comfort & Relaxation!!! is a apartment in Portland, with parking, room for a group, 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,310.

From$187/night
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Higganum House B&B - Portland, CT

Higganum House B&B

B & B, Portland

Higganum House B&B is a b & b in Portland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Higganum House B&B

Higganum House B&B is a b & b in Portland, with 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 breakfast, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,865.

From$224/night
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Higganum House B&B - Portland, CT

Higganum House B&B

B & B, Portland

Higganum House B&B is a b & b in Portland, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Higganum House B&B

Higganum House B&B is a b & b in Portland, with 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 breakfast, free wifi, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,800.

From$224/night
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Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance - Portland, CT

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

B & B, Portland

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance is a b & b in Portland, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance is a b & b in Portland, with parking 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: parking, free parking, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,611.

From$230/night
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Pet-friendly vacation rentals in Portland, CT

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

#2 *Beautiful 1 BR Apartment - Central CT* - Portland, CT

#2 *Beautiful 1 BR Apartment - Central CT*

Apartment, Portland

#2 *Beautiful 1 BR Apartment - Central CT* is a apartment in Portland, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About #2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT* is a apartment in Portland, 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: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,143.

From$163/night
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Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy - Portland, CT

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin, Portland

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy is a cabin in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base…

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About Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy is a cabin in Portland, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,898.

From$196/night
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SPACIOUS AND QUIET - Portland, CT

SPACIOUS AND QUIET

Apartment, Portland

SPACIOUS AND QUIET is a apartment in Portland, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About SPACIOUS AND QUIET

SPACIOUS AND QUIET is a apartment in Portland, 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 $1,378.

From$197/night
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3 BR Apartment Near Wesleyan 202 - Portland, CT

3 BR Apartment Near Wesleyan 202

Apartment, Portland

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

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About 3 BR Apartment Near Wesleyan 202

3 BR Apartment Near Wesleyan 202 is a apartment in Portland, 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 $2,156.

From$308/night
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Vacation rentals with a kitchen in Portland, CT

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

All New Studio apartment in center of town - Portland, CT

All New Studio apartment in center of town

Apartment, Portland

All New Studio apartment in center of town is a apartment in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About All New Studio apartment in center of town

All New Studio apartment in center of town is a apartment in Portland, 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 $1,042.

From$149/night
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Once the old Schools house now a newly furnished Apartment - Portland, CT

Once the old Schools house now a newly furnished Apartment

Holiday Home, Portland

Once the old Schools house now a newly furnished Apartment is a holiday home in Portland, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment is a holiday home in Portland, 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 $1,042.

From$149/night
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Luxury Loft (perfect for business or pleasure) - Portland, CT

Luxury Loft (perfect for business or pleasure)

Apartment, Portland

Luxury Loft (perfect for business or pleasure) is a apartment in Portland, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury Loft (perfect for business or pleasure)

Luxury Loft (perfect for business or pleasure) is a apartment in Portland, 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, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,353.

From$193/night
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Lovely Family sized 3 bedroom Colonial home, close to restaurant. - Portland, CT

Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Holiday Home, Portland

Lovely Family sized 3 bedroom Colonial home, close to restaurant. is a holiday home in Portland, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Lovely Family sized 3 bedroom Colonial home, close to restaurant. is a holiday home in Portland, with parking, 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, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,914.

From$273/night
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Family-friendly vacation rentals in Portland, CT

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

Life on the Farm - Portland, CT

Life on the Farm

Apartment, Portland

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

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About Life on the Farm

Life on the Farm is a apartment in Portland, 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 $1,318.

From$188/night
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Comfy and Equipped for a Small Family - Webster Hill Suite1E - Portland, CT

Comfy and Equipped for a Small Family - Webster Hill Suite1E

Apartment, Portland

Comfy and Equipped for a Small Family - Webster Hill Suite1E is a apartment in Portland, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring…

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About Comfy and Equipped for a Small Family - Webster Hill Suite1E

Comfy and Equipped for a Small Family - Webster Hill Suite1E is a apartment in Portland, with 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 $1,365.

From$195/night
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Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! - Portland, CT

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

Cottage, Portland

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

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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 Portland, 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 $1,545.

From$221/night
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Cozy Lakefront Cottage #6 - Portland, CT

Cozy Lakefront Cottage #6

Cottage, Portland

Cozy Lakefront Cottage #6 is a cottage in Portland. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Cozy Lakefront Cottage #6

Cozy Lakefront Cottage #6 is a cottage in Portland. 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, dryer, ac, air conditioning, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,824.

From$261/night
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